Stunning Water Views from ''Windward'' on the Bay
Wellfleet Vacation Rental - ID 3600

To sum our experience up in a word - WOW. Windward really lived up to our highest expectations!

Starting at the outside and working my way in:

I have to start with the view - ever-changing tides, skies and sun kept us glued to the windows and living on the elevated deck. We had rented two paddle-boards (stored on the community rack a short two minute walk from the house) and had an amazing time exploring that landscape from the water.

The property and landscape around Windward made our long time Cape renting (now owning) friends green with envy. Absolutely classic cape shoreline vegetation, white shell driveway and a hammock just made for warm afternoon gab sessions (our daughter and her friend) and naps (me). Moving closer to the house - the outdoor shower is fully tricked-out with everything we needed. I'm pretty sure that no one took a shower inside the entire two weeks we were there! I even showered outside in the rain - why not?!

The house itself - classic Cape style. Bedrooms (all on the first floor) are cozy and the beds so comfortable with the thick soft mattress toppers we love. My wife and I had to shake ourselves every day when we woke up in the primary bedroom and looked out the big windows at that changing landscape. The primary bathroom almost feels like a ships cabin - there is just the right place for everything and plenty of storage space.

The basement is dry, clean and kitted out with everything we needed for the beach and Cape explorations. There was lots of room to store our extra food and beverages and washer/dryer worked well.

Saving the best for last - the upstairs living space. It worked perfectly for our group of eight family members. Starting in the kitchen - we ended up cooking most of our meals to avoid long waits at restaurants and to get some good pre-dinner cards and cocktails in. The kitchen has anything you could think of - including very sharp knives (a usual pet peeve I have with rentals). The kitchen has the most amazingly deep drawers - if you can't find something, just keep pulling out the drawer and you will find it! The ice maker cranked out ice for us and there were more spices than we could use. Also, the fish light fixture was everyone's favorite!

In the living and dining rooms, there are ample places for everyone to sit including our favorite lounge chair reading nook with it's own little window. Our meals around the dining table were raucous and homey - just what our family loves. The wood ceiling, oriental carpets and decor give off such a warm vibe, almost like being in a fabulous treehouse. Oh, and there are tons of windows that slide open to provide great ventilation - we barely had to use the AC (but when we did, it worked very well).

Finally, the outdoor porch. We used it for shady breakfasts, planning our Cape adventures, grilling out and watching the amazing sunsets. The porch also catches the breezes to keep you cool any time of day.

And our hosts Elisabeth and Douglas are fantastic! We got a great tour at the beginning of our stay where Elisabeth answered all of our questions and pointed out the excellent features of the house. They were quick to respond with any follow up questions during our stay. I can't think of a better situation for visiting the Cape with family and friends - we LOVED our time at Windward!

We stayed here for a week with two families. We are lucky enough to stayed here the second week of July. The house was very clean and had lots of amenities. I have never stayed at a rental with so many things provided for you. The views from the balcony were amazing. The owner had great communication and great recommendations. I would most definitely stay here again.
Thank you for a lovely time

Our family, 8 of us, stayed at Windward for a week from July 4th through the 11th, 2026. It was a great visit, though we had a day and a half of rain, but the place had games, books and things to do even if we were inside. The amenities were all very nice and above and beyond any other rental we've done in the past. Just a very pleasant and relaxing week.

Our time at Windward was perfect in every respect. I'm hard to please when it comes to vacations, and I do a LOT of research before committing to a rental. Windward - and our gracious hosts - delivered on every one of my requirements. The property is charming and full of character, with the kind of view that had us spending lazy hours on the deck watching the tides change. Beautiful natural light, lovely sunsets, and so many comfortable places to sit or lounge while enjoying the setting. The home was scrupulously clean, better than any property we've rented. The beds and linens were of excellent quality, with an assortment of bed pillows from soft to firm to suit every taste. Each of us was provided a tote with essentials, including sunscreen, bug spray, aloe, and toiletries - and each of the 3 bathrooms was also well equipped with everything (and more) we needed. I was determined not to use the kitchen during our vacation, but was nonetheless inspired to make some fun breakfasts. Our lovely hosts provided every imaginable spice, Bisquick, sugar, maple syrup, excellent coffee, and every cooking/baking implement. The neighborhood is peaceful and private and there were long stretches of time when we only heard the wind in trees. Elisabeth and Douglas have considered their guests' every need, want, and comfort during their stay. They earned an unprecedented 10/10 from these hard-to-please travelers (including two teens!). And Wellfleet is a great central location to explore everything Cape Cod has to offer, from P'town to Chatham and Harwichport, swimming in the kettle ponds to walking along the massive dunes and observing seal pods, marsh trails to boardwalks, and the food! So much to do and see (or not). We're looking forward to our next visit to this special place. Heartfelt thanks to our hosts for this unforgettable and relaxing week together as a family.

We truly enjoyed our 2 week stay at Windward this past June, 2026. The entire house, and most especially the kitchen, was very well appointed, the best we have ever seen. All we needed was a toothbrush and our clothing. The sunsets were stunning, the view was spectacular, it was extremely quiet and peaceful, sitting on the deck brought you to your zen place. The owners were extremely helpful with very good communication. We definitely would consider returning. Thank you for a lovely and relaxing trip.

I stayed at Windward mid-May to mid-June, 2026. The view of Blackfish Creek as it flows into Cape Cod Bay is stunning and endlessly changing with the tide. The house, a custom built post and beam is beautiful and comfortable. It is well appointed and generously supplied. The owners who live in Wellfleet are most accomodating, helpful, and pleasant. My stay at Windward was a genuine escape

We had a wonderful week at this exceptionally well-crafted and well-provisioned house. The post and beam construction exposes woodwork and rafters throughout, making the house a true work of art. The custom kitchen is amazing and fully supplied with every conceivable gadget and utensil.
The owners provide every amenity throughout: the shelves are stocked with books and novels, the bathrooms and bedrooms are provisioned with linens and towels, and there is an indulgent outside shower and other niceties that clearly indicate the care and attention to detail paid by the owners.
The layout of the house provides four cozy bedrooms on the first floor with a central staircase to the upper floor with kitchen, dining room, living room and lovely deck providing a spectacular view overlooking Blackfish Creek. As this is a west-facing view, the sunsets are spectacular.
We took a number of lovely long walks on trails directly accessible from the house leading to Old Wharf Point and Cape Cod Bay. Also, the Wellfleet Audubon Wildlife Sanctuary is nearby and provides plenty of diversion for bird and nature lovers.
We enjoyed our week at Windward and are looking forward to returning next year.

Seven members of our family had an incredible and unforgettable stay at this stunning home! The house was immaculate, thoughtfully (and fully) stocked with beach and personal care items, and decorated with beautiful things. The beds were very comfortable. We enjoyed the spacious outdoor shower, and a convenient foot rinse station after visiting the beach. The views of the water and sunsets were breathtaking from many spots inside and outside the house. We were able to store and use our kayaks a short walk from the house. The home is a short drive from the Drive-in theater; town; Wellfleet harbor; and pond, ocean, and bay beaches. The owners are very responsive, and gave us a tour of the house at the beginning of our stay. Highly recommend!

This is our fourth year renting Windward and I believe our second time renting for two weeks. As always the house was clean and extremely well stocked with hosts ensuring you just need to bring yourself and your clothes! The hosts make upgrades every year so the house is always in the best shape. The house was perfect for hosting various family members over the two weeks with enough space for lounging that no one is ever in anyone else's way. The views, especially the sunsets, are stunning. Very peaceful location yet close to everything on the Outer Cape.

The Windward house sits on a perch overlooking Blackfish Creek, Fox Island Conservation, and all the way out to the Great Island's cliffs. It is a slice of heaven. The view is mesmerizing! This post and beam house is beautifully constructed with a layout that takes advantage of the views. Our family was very comfortable in the 4 bedrooms with 2.5 bathrooms along with the best outdoor shower. The de-sanding station at the back door was used every day. The house is extremely well supplied with anything you would need for your stay. We had not been to the Old Wharf neighborhood as we have rented on Indian Neck for many years. We loved this part of Wellfleet. It is a gem. Every day we walked down to the point for a swim. Elisabeth and Douglas were attentive hosts and have set up an incredible vacation spot! Thank you!!

We had a wonderful week at this beautifully maintained home. Everything was spotless, tastefully decorated, and clearly cared for with love. The house was stocked with absolutely everything you could possibly need — from plenty of fresh towels to a fully equipped kitchen. Because the home is so nicely appointed, families with young children will want to be mindful, but it's a lovely space for creating special memories together.

The location was great. A short walk took us to a nearby marsh area full of fascinating ocean wildlife — we spotted crabs, shorebirds, and other beautiful coastal creatures. Wellfleet has many activities in addition to numerous beaches such as an animal sanctuary and drive-in movie theatre.

This is truly a perfect home for a relaxing family getaway.

We have vacationed in Wellfleet every summer for nearly 20 years, staying in various weekly rentals. Windward is far and away the best and our favorite. We will stay at this lovely home again and again.
The home is immaculately maintained, beautifully furnished and full of charm and character. The house is situated up high with spectacular bayside water views and sunrises and sunsets without comparison. The hosts/homeowners, Douglas and Elizabeth, have equipped the home thoughtfully we every possible convenience and amenity. Over the years, we have from time to time had to bring everything with us from sheets to cleaning supplies along with all necessary for a week stay at the beach. Not so at Windward! What a joy to have every essential at our fingertips. Just bring food and clothes.
The house itself is lovely. Each bedroom is comfortable and cozy. Home rather than beach like. The living area is generous in size, equipped with modern conveniences, and decorated tastefully and winsomely.
Windward is a home built with care and maintained with an extraordinary level of attention to every detail. Information about the area and activities nearby abounds. There is also an extensive collection of books -- some about the Cape and Wellfleet and plenty for a summer beach read. There is an impressive collection of spices and basics -- flour, sugar, tea, coffee -- and every sort of kitchen gadget, cooking tool and serving ware. Plus, the kitchen is a gourmet's dream with high end appliances and plenty of space to prep. The adjoining dining room is open and framed by that spectacular water view. The master bedroom, a floor below, also looks out toward the water. Quite a way to wake each morning...if you have the good fortune to land in the master bedroom. If not, have your morning coffee on the deck. Same view and fresh air
Windward is, in a word, wonderful. Don't hesitate to arrange a stay if you have the chance.

We had an absolutely wonderful stay at Windward! The location couldn't be better - close to everything yet peaceful, with gorgeous water views that make every day feel magical. The home itself is spacious, with large, comfortable rooms that are impeccably clean and meticulously maintained. It's beautifully decorated with local artwork, giving it a warm and authentic Cape Cod feel. The owners have truly thought of everything - every amenity you could possible need is stocked and ready. On top of that, the hosts are fantastic, responding immediately to any questions or requests. This is the kind of place you look forward to coming back to year after year.

If you're looking for a restful retreat with lovely sunset views over the water this house fits the bill. It's an updated and well equipped vacation sanctuary. Clean as a whistled and well maintained and stocked with anything you could wish for! The owners take great pride in this place for good reason. Perfect for our family gathering which included a toddler. You will NOT regret your decision to stay at Windward!

This was our third summer staying at Windward, and it continues to exceed expectations. The owners clearly take pride in the home and consistently attend to every detail. The house and grounds are immaculate, with thoughtful touches throughout that make it feel both luxurious and welcoming.

The setting is peaceful and beautiful, with a nearby marsh that's perfect for kayaking and paddle boarding—something we look forward to every year. The house is ideally located: just a short drive to the town center and some of the most stunning beaches on the Cape.

Inside, the kitchen is a dream for anyone who enjoys cooking. It's incredibly well stocked with everything you could need—high-quality pots and pans, blenders, utensils, and even an impressive selection of spices and pantry staples. The open common area is perfect for group gatherings, and the deck offers gorgeous views and a lovely spot to unwind at the end of the day.

Windward has truly become a special place for our family. We hope to return next summer.

Our stay in this fabulous property included 5 women, from all parts of the country. The magnificent view, and the traditional Cape Cod decor gave them all a great introduction to what The Cape is all about. The house has everything you could ever need! And I mean, EVERYTHING! High end beach chairs, beach games, scores of puzzles, beautiful glassware for the libation of your choice….and, not only are the bathrooms equipped with hairdryers, toothpaste, etc, but each person was left a shower caddy with shampoo, body wash, bug spray, a loofah sponge….and more! The deck is the perfect spot to take in the ever changing view. And, if you can get yourself to leave it, just a short drive will get you to some beautiful beaches. We also enjoyed the short drive to Ptown for shopping and drinks. Douglas and Elisabeth are incredible hosts. What a gem!!

From the start...great communication. The home owners provide a full packet prior to arrival and there are Plenty of brochures in the home for activities, shopping, dining and more. Very welcoming and warm home, well appointed with toiletrie provisions, games and every cooking amenity you could need.

Our family including our Old English Bulldog which stayed on the property.

The House itself...you can tell lots of thought and love, appreciation for the surrounding area and expert craftsmanship went into this house. The house pays homage to local artists.

Plenty of areas both inside and outside the house to relax. Sit under the trees in the front yard swinging on the hammock, watch the sunset on the upper deck, or outsode the master bedroom, or read a book on the chaise in the dining room.

Excellent location. While off the beaten path also very close to all necessities, ocean and bay beaches are minites away. Lots of great local eateries nearby...30 minutes less from Provincetown. Tons of shops, antique shops nearby.

Great trails, wildlife sanctuaries, fishing, dock life all nearby.

We will be inquiring about a weeks stay next year.

Our family really truly enjoyed this one...it was so much fun!

Our three adult children and their significant others joined us for a week at Windward. We were all quite comfortable. When we weren't exploring the Cape we were cooking, playing games, puzzling or watching movies at the house. This home has many gathering areas as well as several quiet reading nooks, perfect for our group. When we are together, we enjoy cooking, never have we stayed at a vacation home with such a well stocked kitchen. The views from the home are stunning and all the activities we were interested in doing were easily accessible from the home's location. We hope to return in the future.

This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained house to have an exceptional vacation. The house is well equipped, so much so that you truly only need to bring your clothes! All the beds are very comfortable, the kitchen extremely well equipped and there is plenty of room for 8 adults to spread out. The location is peaceful with gorgeous sunset views and convenient to everything on the outer Cape. We will definitely be back for year 4!

We were celebrating my husband's 75th birthday and wanted to do something special that could include his four grown children and three-year-old granddaughter. Windward was the perfect solution for us! I grew up in Massachusetts and now live in the mountain west. It was especially important for me to show to my family the beauty of Cape Cod where I spent a lot of time through the years.Windward has so much character, so much loving detail in every aspect of the home. The careful architecture and style, the fully laid out kitchen, the deck with sublime views of the bay, the outdoor showers, the comfy beds, the beach chairs, towels and toys and they aren't kidding when they say that you only need to bring your clothes! Everything else is supplied. Douglas and Elizabeth leave detailed instructions both at the home and they send them in the mail to you so you have plenty of time to plan. It is completely secluded there and very quiet. And yet it is only a five minute drive into the charming town of Wellfleet, loaded with galleries, shops and restaurants. It is also a short drive to Provincetown where we went on a Whale Watch. We also visited the local theatre, and there's more than one! It's professional theatre of the highest quality. The landlords are available to take care of any concerns you might have. They are close by and always answer your communications. And they are super nice people. By the way, don't go grocery shopping until you see all the kitchen supplies that are already there, from coffee to a huge array of spices, olive oil, etc. And it is a cook's kitchen for sure with all the utensils you need. Also, a great grill is available on the deck! I can't say enough about Windward. We recommend it to anyone wanting to experience the authentic Cape Cod.

This was our first stay at Windward. We were a group of 8, including three teenagers. The home is clean, comfortable and the view is fabulous, especially at sunset. Easy access to the bay beach via nearby Indian Nauset Trail. Very short drive to access the water to launch kayaks. The neighborhood is quiet and the location is convenient to popular Wellfleet beaches, restaurants and the center of town.
Douglas and Elisabeth generously provided beach items which saved space when packing the cars. They also provide personal items for everyone, including sunscreen, bug spray, toiletries and shower items.
We will definitely consider Windward again next time we visit Cape Cod.

We spent two glorious weeks at Windward with our family - 4 adults, 2 teens, and two dogs. The house was perfect for our group - it was well stocked, very clean and comfortable. The craftsmanship is unique and high quality - the upstairs living area provided amazing views of the marsh, tides, and sunsets. There is a well-stocked gourmet kitchen. The outdoor shower is fabulous - the best we have encountered on the Cape. There is easy access to quiet roads and trails for walking, including along Blackfish Creek. We enjoyed meeting the incredibly nice and responsive owners. We would definitely consider a return visit.

Our family recently returned from another perfect 2 week stay at Windward. The house, like last year, is immaculate and incredibly well-appointed. Douglas and Elisabeth are wonderfully attentive hosts and made sure we had everything we needed, and more. It is clear they put a lot of thought and care into providing a comfortable and luxurious stay for their guests. HIghlights of this beautiful cottage nestled in Wellfleet were breathtaking views of the marsh at sunrise and sunset, taken in from the expansive deck, and kayaking in the marsh. Note - Jack's boat rentals delivers boats right down to the marsh for Windward guests. We have already booked our stay at Windward for summer 2025 and cannot wait to be back!

We enjoyed our stay in this well appointed and beautiful house. Kitchen, bathrooms, and laundry room were all stocked with supplies. Sunsets are spectacular! Having a rack for the kayaks we rented at the end of the nearby walking path was very convenient. Wellfleet is quintessential Cape Cod with an abundance of fantastic beaches and restaurants.

I just spent a very relaxing week at Windward. The home is equipped with everything one could possibly need with all the comforts of home. My family loved the deck and the wonderful ever-changing views of Blackfish Creek. I spent a lot of time in the reading nook with a beautiful view of the water. Even if someone was watching tv, the nook was quiet, comfortable, and peaceful. The home has space for everyone with a thoughtful layout. This is the perfect home for a family to spend time together as well as relax in your own space. The beds are amazingly comfortable too! The quiet surroundings and a walk along Nauset Trail adds to the charm of this splendid location.

As advertised this house has an amazing view of the Wellfleet bay area. The sunsets can be amazing. However there are some issues with the house and the owners that you should be aware of. First let me say the owner Elisabeth emailed me on two occasions that she would return my security deposit after I wrote a 5 star review and she detailed some of the requested points I should emphasize. She may deny much of this but I have the emails.
The amenities mention a "screened in porch". There is no screened in porch , instead a careful reading mentions "The living area is essentially a huge screened porch ". The. pictures are accurate in that two walls of each living area have windows with screens. The porch area is totally open and at sunset , the mosquitos and gnats are to be expected as always on the Cape. The house is very cluttered and the living spaces are all small. I suspect the entire house is less than 2000 square feet (common on the Cape). The bathrooms are very nice as is the outside shower. The kitchen is very well appointed and the owners go out of their way to keep all items stocked. The airconditioning downstairs is borderline for hot cape weeks and the warning is not to turn the thermostat to less than 72 degrees or the system will freeze. One of the bedrooms does not cool adequately at this setting. We were warned about the upstairs unit failing and warned again not to set below 72 . On the hot days it struggled but apparently it will be replaced. It is not a good house for a toddler (and we had one) as the owners have many items that are breakable . This should be noted . Overall I think for 4-6 adults, the house is quite beautiful and well appointed.
However there is a caveat. As I intimated above, the owner Elisabeth is a very unusual character. She will undoubtedly have many rebuttals to what I say , as she already has told me that we were the 'worst renters" she has ever had. This was well before we left . We were offered three rooms for the "crib". but on arrival,we were told that we would not be allowed to move it . Only she could move it. Elisabeth insisted on meeting with us on arrival for 45 minutes detailing everything, She later complained that I changed the time from 4pm to 5pm arrival (giving her 24 hours notice). She and her husband came by everyday to water plants and on one occasion entered the house without knocking. She warned me to put the umbrella down on the porch to avoid wind knocking it down. We left it up for an hour one evening and a totally unexpected wind gust knocked it over , broke it and cut a screen. I offered to replace both but she insisted on taking care of it along with her husband. I agreed to pay for the damages . She wanted to enter the house but I said I would take the screen down myself , which I delivered to her. She was literally inconsolable . I did not want to let her in to the house because the toddler was sleeping and and some things had been moved around .We left the house in excellent shape with everything put in its place. I asked Elisabeth to detail any damages she found . She exaggerated findings , like claiming flimsy gates that were useless anyway , required 30 minutes for her husband to repair. I had done it several times in 2 minutes. She claimed they needed additional cleaners. The house was in =excellent shape . The dogs were not allowed upstairs and I did a first vacuuming of the downstairs before I left. First , Elisabeth said I should determine the damages (I offered 150 for the umbrella and 50 for a shade she first claimed we destroyed and later said we were not responsible for). She then totally backtracked and decided to buy a 500.00 umbrella and charge 185 for other items . She then offered a 50% discount which I accepted and paid (338 total). She had long emails with multiple ad hominum attacks. Lets just say Elisabeth is omnipresent and she is highly irascible. Be forewarned.

Our family returned to this cottage a second season because of the unsurpassed view and peaceful surroundings. The upstairs contains a fully-equipped kitchen with modern appliances. Since the cottage is minutes from Hatch's fish market, we chose to cook fresh seafood every evening. We enjoyed sitting on the upstairs deck every morning with our coffee and to view the wonderful sunsets. The king sized beds on the lower level are so comfortable we all slept comfortably from the first night. The location also makes it easy to bicycle from the cottage to the rail trail, the Old Wharf and ocean view drive.

We spent a wonderful week at Windward. The water views and sunsets were unbelievable. The post and beam style upside down house was beautiful. There were fresh cut flowered in every room. Also, potted plants that didn't need watering. The house was extremely clean and the kitchen had every utensil, pot and pan, bowl, and spices, etc. you would ever need. The house is in close proximity to bay, ocean, and pond beaches. Also close by were restaurants, grocery stores, galleries, shops, boutiques, rail trail, and Audubon Sanctuary. Doug and Elisabeth were available at any time. My husband and I spent the most relaxing week in a beautiful setting.

Four of us had the immense pleasure of staying at Windward in September of this year. The house is simply charming and obviously well loved and cared for by its owners. It's location on the bay allows for spectacular views of the water and we enjoyed many evening meals on the deck while admiring unfailingly gorgeous sunsets. The floor plan of the house is reversed so that the numerous bedrooms downstairs allow for optimal views of the bay in the ample yet cozy living area upstairs. My favorite inside spot was the "magical" readind nook complete with upholstered chaise lounge and a small window overlooking the bay! Our hosts were extremely accomodating in every way. The kitchen was well stocked for cooking and serving meals and included not just complimentary coffee but also basic cooking needs such as sugar, flour, oil and a vast array of spices. In addition, each bedroom was thoughfully supplied with shower caddies full of useful toiletries for the newly installed outdoor shower. There were even small tubes of toothpaste in each remodeled bathroom - just in case you forgot! My favorite welcoming touch, however, were the fresh flower arrangments in several of the rooms! We found the location of the house to be ideal - close to town, to numerous beaches, to local shops, galleries and restaurants. Next time, (and we hope to return!) we will avail ourselves of the nearby bike trail as well.

After spending one week at Windward in 2022, we decided it wasn't enough and booked two weeks in 2023 and thrilled again with our experience. The property is lovingly cared for by the owners and every amenity is taken care of. The kitchen is wonderfully stocked with essentials, there are plenty of towels and beach towels and all the beach items you could possibly need. I particularly like the comfort of Windward...there is plenty of space for everyone to spread out and not be on top of each other and many cozy options for curling up to read a good book, watch the gorgeous sunsets, the ever changing tidal marsh views or tune out to TV. I also appreciate the modern bathrooms and the TWO outdoor shower spaces. The location is perfect...very quiet and peaceful but a short ride to restaurants, ocean and bay beaches and the Wellfleet Kettle Ponds. We even brought our bikes this year and easily biked to the Cape Cod Rail Trail.
Elisabeth and Douglas are super conscientious hosts and want to ensure that your stay has everything you need for comfort and relaxation.

My family recently had the privilege of staying at this lovely home, and it truly exceeded all expectations. From the moment we arrived, we were greeted by the most breathtaking sunsets which we enjoyed every evening.

The rental itself was a source of comfort and convenience. It was abundantly clear that the owners had put a lot of thought and care into making sure every guest's needs were met. The place was incredibly well-stocked – from the kitchen essentials to the bathroom toiletries. This attention to detail made our stay so much more enjoyable, as we didn't have to worry about running out for basic supplies.

What truly sets this vacation rental apart is its prime location right on the bay. The proximity to the bike trail was another highlight – we spent our days exploring the area on two wheels, surrounded by nature's beauty. It was a quick ride to the beautiful Marconi Beach. Our daughter and son-in-law were even able to travel there by bike from the Provincetown ferry.

But what truly resonated with us was the care that seemed to have been poured into every nook and cranny of this place. It's not every day that you come across a vacation rental that manages to combine comfort with warmth, but this one pulled it off seamlessly.

In conclusion, our stay at this vacation rental was wonderful. The stunning sunsets, the well-thought-out amenities, the bay-side location, and the evident passion that went into its creation made it a true gem. If you're looking for a place to unwind, reconnect with nature, and bask in the comfort of a home away from home, this rental should be your top choice.

The owners of Windward went above and beyond to ensure we had an unforgettable two week vacation. First, the setting on the water is spectacular with views for days! The location is fantastic- close to beaches and a quick drive to town. The house is completely stocked with anything and everything you would need. The kitchen has anything a gourmet chef would need, including dozens of spices. We were also provided with coffee pods for the Keurig and new coffee for the regular coffeemaker! The bedrooms all had clean sheets and towels, plus fully stocked bathroom caddies for each person that included new shampoo, soap, bug spray, sunscreen, and many other items. The home is also stocked with everything you need for the beach including beach towels, blankets, chairs, umbrellas, coolers, etc. The owners are readily available for any questions or concerns and could not be nicer. The house had vases of fresh cut flowers upon our arrival in every room! The decor is cozy and comfortable, with beautifully updated bathrooms and kitchen. The outdoor spaces are also great, and there are very handy outdoor lines to hang towels after a day at the beach. We loved the large, newer outdoor shower as well. The owners have thought of everything and we cannot wait to return.

My extended family just spent a spectacular week at Windward. It is even better in real life than in photos. Perfect setting where you can watch the sun move across the marsh and water all day. Super comfortable and charming bedrooms, living spaces. Spectacular (everything you need ) chef's kitchen and lots of outdoor spaces where you can seek shelter from
Sun- or sunbathe depending on your preference. Elisabeth and Douglas are the perfect hosts. It is clear how much they cherish Windward and you will too after spending time there. Wellfleet delights with its ocean, bay beaches and lovely ponds. Perfect spot - enjoy!

This was truly the most magical vacation home we have ever stayed in. The views alone are enough to recommend this home, but there is much, much more. The house is fully stocked with absolutely everything you could ever want or need - from cooking supplies to towels, extra blankets, plenty of beach reads, and even a personal caddy for every guest that includes all the things you might forget, like sunscreen, shampoo, aloe, and razors. The decor is casual and elegant with plenty of seating for a spectacular view of the marsh - whether from inside on a cloudy day or sitting on the deck, or on the hammock in the ample front yard. The owners have thought of everything to make guests feel welcomed and cared for. We have already booked our stay for next summer and cannot wait to return.

We recently stayed at Windward for a week, 8 adults, and we had such an amazing time. Windward really goes above and beyond to make sure guests feel well-cared for. The property is impeccable, beautifully furnished, and comes with everything you might possibly want or need for a Cape vacation. The kitchen provided everything for grilling, cooking, baking, or even ordering in! We didn't have to buy any staples like paper towel or seasonings - it's all right there! The bathrooms were fully stocked with necessities, and very clean! A really beautiful touch is an outdoor shower kit provided to each guest, complete with shampoo, sunscreen, soap, etc. - such a wonderful and welcoming way to greet guests! The homeowners have gone above and beyond in the extra features they've added to the property to make guests feel so at home. For us, one of the best parts was not having to pack anything from home to bring to the beach! The property comes with beach chairs, umbrellas, games, towels, coolers, and anything else you might possible need or want to really enjoy the local beaches, bay and oceanside. The views and sunsets from Windward's deck are stunning, and a little path brings you right down to a small strip of beach that is private and cozy. I can't recommend Windward enough! You definitely won't be disappointed!

Wonderful family vacation, clean, charming and great views! Slept extended family of 8 very well. We walked to Marconi Beach, a lovely 2.5 mile walk everyday! That was a big surprise it was so close. Very close to bike trail too. Lovely place and really nice bathrooms and kitchen too.

On a quiet walk in Spring of 2022,we came upon Windward cottage. We and admiration of the architecture and view of the marsh. We found this home listing and immediately contacted the owner to reserve for Sprng 2023.
Our wonder expanded when we first entered the cottage on June 3, 2023. The views of the marsh from the living areas and master bedroom are unsurpassed. Our family of six decided to prepare dinner in the fully-equipped, well-appointed kitchen every evening. When it was my turn to prepare dinner, I would turn on classical music and dreamily take my time in the moment, while looking at the view. Hatch's Fish and Produce is nearby in the village of Wellfleet. Most of their seafood is fresh daily, as well as oysters from their own beds.
A rainbow appeared over the marsh our first morning. Days were spent bicycling and hiking the known and less known trails around Wellfleet, as well as gazing at the ocean from the town beaches. The ponds are nearby and offer swimming. We brought a kayak, which can be launched in some ponds and the marsh below the cottage.
Evenings were spent reading or working puzzles, listening to the wind and sometimes the rain. We slept well in the comfortable beds. We all appreciated the on-suite bathroom and shower, extra nearby bathroom with tub and shower, upstairs toilet near the living area, and outdoor shower. Linens and towels are provided, as well as a washer and dryer.
There are plenty of restaurants, shops and art galleries nearby, as well as theatre, and the Wellfleet Drive-in. Our daughter and her fiance biked from the cottage to the Provincelands and back in four hours. We discover something new every year, and Windward is a joy to return to each day.

What a vacation this was! Douglas and Elisabeth gave us extensive information on the house and town before we even arrived. Upon our arrival, Elisabeth greeted us warmly, had a few thoughtful "welcome to our home" gifts, gave us a full tour of the house, and even strolled the neighborhood with us to show us where the trails to the water were. They checked in to be sure we were happy with everything.

The house is even better than the photos show. There are so many nice little decorating touches that you just can't capture in a photograph. It is all sea themed and often Wellfleet themed, with paintings and sculptures by local artists. It manages to be roomy and cozy at the same time. The post and beam construction surrounds you with beautiful wood. The kitchen is incredibly well stocked. The custom designed cabinets make excellent use of space, the appliances are new, and whatever you need is there and organized meticulously. The bedrooms are charming, the beds were very comfortable, linens and towels are supplied. There was ample seating in both the dining room and living room, and no less than four outside sitting areas. The views of the water and the sunsets are spectacular. If you don't like sand, just sit on the deck, enjoy the sun, and be surrounded by water views. The neighborhood was quiet and delightful to stroll and bike. The woodworking in the master bath is simply beautiful and all the bathrooms look like they have just been remodeled. Even the fixtures are elegant. There is also a very nice outdoor shower. Everything is spotless.

May can be a bit unpredictable, but we were blessed with a spectacular week of sunny weather in the 60's and 70's. There are lovely trails (in Wellfleet at Marconi, in the Province Lands, and the Audubon Sanctuary), numerous kayaking sites, a wonderful gym called Heart Core, Catholic Masses are available in Wellfleet, P-town and Orleans, lovely bay and ocean beaches, and of course the Cape Cod Rail Trail. We were able to find gluten free fare at Montano's, Three Fools, the Rail, Far Land Provisions and PB Boulangerie. Wellfleet Marketplace is great store that has just about everything and is oozing with local flavor!

This vacation was picture perfect.

Windward was everything we expected and more. Very clean and great communication with the owners. The views are spectacular & close to beaches. Wellfleet is charming with wonderful shops and restaurants.

Watching the ever changing landscape of the tidal marsh, gorgeous sunset cocktail hour on the deck, plenty of comfy couches for lounging and reading and every detail thought of sums up our week. Elisabeth and Doug have created a beautiful oasis and are super conscientious in ensuring you have the best, more carefree vacation at their house. This is the 7th house I've rented on the Cape over the last 20 years and definitely the best. Honestly the photos don't capture the specialness of this home.

Our family recently spent a lovely week at Windward in Wellfleet. We were a group of 8 people, 4 couples, as well as a very happy Bichon Frise. We all enjoyed the space, the grounds, and the area. The home was beautiful and immaculately clean and well cared for. The owners were very responsive both in advance of the vacation, as well as during our stay as need arose. We all found the views to be just spectacular ... from the deck, the grounds, and from several rooms facing the water. We've rented in Wellfleet for nearly 30 years and the sunset view from Windward is definitely the best we've ever had.

If you live for amazing Cape views this is the house for you. With views on both levels, the experience staying for a week was just an amazing delight. For those concerned with other essential things like comfortable beds and a well-stocked kitchen., you have also found the right place. Top of the line appliances and a fully stocked kitchen are prime features of this kitchen. There is also a really nice deck that overlooks the Bay. Finally, the house is very well stocked with beach equipment -- umbrellas, chairs and much much more.

The house was immaculate and met all our needs. We had almost all our family staying at the house, which easily accommodated everyone. Every amenity you could think of, whether staying at the house or spending a day at the beach was thought of.

The surrounding property with a view overlooking an inlet to Cape Cod Bay was breathtaking, especially the sunsets. Elisabeth and Douglas were very helpful in providing information about the best beaches and restaurants.

The house is within short driving distance to beaches, restaurants and the town, with all its art and craft galleries.

I loved our visit and have already discussed with them a return stay next year.

My wife and I stayed at Windward for seven nights at the beginning of July. In one word, our experience was "exceptional." Elisabeth and Doug were wonderful, attentive, hosts who provided us with all the information about Windward that made the week fly by.

So the sunsets from the deck are amazingly beautiful; the changes in the bay waters are a wonder to behold; the accoutrements in the house are very tastefully and aesthetically pleasing; very user-friendly kitchen, SPOTLESS house, quiet, and serene. Close to restaurants and five minute drive to center Wellfleet. We highly recommend staying at Windward. What a find!

My husband and myself along with our 4 adult children had the pleasure of renting Windward the last week in June. We have traveled and rented homes often and this was by far the most organized and well stocked home we ever rented. From bedding to beach toys to a state of the art stocked kitchen they had it all!
There is nothing you needed to bring. My two Favorite parts were how everything in the house was labeled and how each room had shower caddies for each person filled with toiletries, sunscreen, after sun lotion, razors, and so much more.

Of course the icing on the cake was the most beautiful views overlooking the water along with breathtaking sunsets.

Elisabeth and Douglas supplied us with so much literature regarding restaurants, beaches , ice cream places, cape cod history and more. They were easy to communicate with before and during our week visit and were available to help us the when asked. They even held on to our daughters bathing suit that we left behind so we could get it back!

Thank you for opening your beautiful home to renters and we look forward to renting again.

Chong's from New Jersey

Wow…..That is the only word to describe Windward! We vacationed with a group of seven family members (all adults) and found the stay so inviting, cozy, CLEAN, and beautiful.

The bay is interesting and entertaining! The proximity to great Ocean Beaches was perfect for our group! Make sure you take a moment during your stay to look at how this home is built. Care went into every beam, floor board, nook and cranny. Thank you Elizabeth and Douglas for a wonderful family vacay!

If you are looking for a clean, cozy, perfectly quirky home on the coast, Windward is a wonderful option. The homeowners have taken great care to provide a fully loaded home, making packing easy. Access to laundry facilities makes unpacking back home even easier. We traveled with my parents and my two children. Windward is large enough to provide privacy for all but quaint enough to make some wonderful memories all together. Its location in Wellfleet is perfect, being close to many National Seashore beaches, tasty restaurants and outdoor activities (biking, golfing, hiking, etc.) I highly recommend Windward!

I booked Windward in early January. Having family from the Cape, we felt it was time to get back "home" even if only for a week. I came upon Windward as I've used this booking site in the past and have never been disappointed. I'll list the pros and the cons.

Pros: location is excellent for those who like to be closer to PTown, Nat'l Seashore, and a bit less craziness the Cape can have! The house is very well stocked with kitchen requirements, extremely comfortable, organized (something I appreciate!), and the sunsets are glorious! The house matches the pictures on the website; quincentennial cape cod appeal. We loved the house.

Cons: We went in early June when ticks are just waking up looking for hosts. Thanks goodness our small non-shedding dog is white! I am used to doing tick checks living in a mountainous area, but the ticks were pretty bad. Spraying the grassy area around the house would help, but may not be allowed for conservation purposes. We all did tick checks and managed it.

Too much contact prior to arrival, and during stay with owners. I appreciate the owners being selective with whom they rent to. I spoke with the owner, Elisabeth, for over an hour when interested in booking Windward, we were sent a 17 page instruction booklet, asked to have a half hour conversation day before we arrived, along with being asked for an hour in person orientation upon arrival. Too much and not necessary. It felt like a lot of "work" just to begin our vacation. This regiment might be something to consider changing. It felt a tad intrusive.


All in all, we had a lovely time. The owners of Windward love their home, and it shows.

Windward is a lovely home with the most beautiful views. The kitchen has everything you will need and you can watch the gorgeous sunsets from the deck or from the living room and dining room. Owners are very responsive and respectful of guests' privacy. Location is lovely - beautiful walk on dirt roads to the bay; close to the best French bakery on the Cape; very close to Marconi Beach and an easy ride into Wellfleet or Provincetown.

I can't think of a better place to spend a week on Cape Cod than at Windward. Located on a tidal marsh off of a quiet dirt road, the setting felt remote and yet was only minutes to beaches,trails, restaurants and galleries. The house itself was charming, warm, and rustic - beautifully designed and maintained. The furniture was lovely, and the kitchen was equipped with everything you can think of. The deck, which overlooks the marsh, (as do most of the rooms in the house) was the perfect place to eat a meal, watch the sunset and just relax.
 
Elisabeth sent us lots of information about Wellfleet even before we arrived, and clearly attends to every detail to ensure a wonderful vacation. We would definitely stay here again.
 

This was my second year returning to Windward for an October stay and I couldn't be more happy with this home. The galleries and restaurants in the area are exactly what I wanted in visiting Wellfleet although I spent more days than expecting in the home because I did not want to leave! The overall cleanliness and comfort of the home is unmatched and sets the standard for what I expect in a vacation rental. The sunsets are amazing, the weather was perfect, the memories were unforgettable.

Can't wait to come back year after year with my family. We have found our Cape Cod vacation home. Well done Elisabeth and Doug.

This was our second October visit to Windward - and it was just as splendid as the first.

The amenities at this home are beyond comparison to anywhere else that we have stayed. Beautiful linens, showers that make you linger, plentiful fluffy towels, bathroom cabinets filled with everything you could possibly need, and spices from A to Z lined up on a wall shelf in the gourmet kitchen, (which, by the way, includes every appliance and utensil you can think of.)

The warmth and coziness of this beautiful home is felt every time you turn around and find some special touch that Elisabeth has added, obviously with great thought and care. Lovely!
Just bring a change of clothes and you are good to go!

In addition to the four beautifully appointed bedrooms on the first floor, it would be impossible to write about Windward without mentioning the stunning water views and truly awe inspiring sunsets that we were lucky enough to enjoy every evening from the deck with a glass or two of wine. We were out and about every day, as there is so much to offer from this location, but were always sure to be back home for the sunset. On the kitchen island, you will find a book that will guide you to the most wonderful walking trails on the Cape, many of which are just a short distance from Windward.

Thank you Elisabeth and Doug! You are such kind and welcoming people, and your home reflects this in every way. Windward offers a unique feeling of comfort, peace, and solitude - something we can all use a little of these days. We look forward to returning!

I can't say enough about this beautiful property. I have been renting properties at the Cape for the last 30 plus years and Windward is by far the best home I have had the pleasure to rent. Elizabeth's attention to detail to make her renter's comfortable is beyond amazing. I will definitely be renting again in the future. If there was a 6 star I would assign it to Elizabeth, Doug and Windward. Cheryl

The Windward cottage was absolutely wonderful!
We were at home the minute we stepped through the front door. The indoor space was beautiful and the outdoor space, everything we could hope for. Our hosts attention to detail was incredible. We will return! Thank you Elizabeth and Doug

Windward was PERFECTION in every way! The house itself is a gem - immaculate and beautifully maintained. The furnishings and decor have been hand selected over the years and are both comfortable and lovely. The layout was perfect for our party of 7 including adult children and extended family, with many spaces indoors and out for us to gather in large or small groups.

The hosts are amazing, anticipating every need of their vacationers and stocking the house accordingly, as well as available to answer any questions we had before and during our stay. The kitchen is a cook's dream! The views are truly incredible ... our favorite moments each day were gathering on the large deck and viewing the spectacular, ever changing sunset and tides. Windward is truly special.

Well...once again, a wonderful vacation centered around a phenomenal rental property. Meticulously clean, stocked with all the vacation items you need (no hyperbole here), and the photographs don't do the actual view justice. This is a property that absolutely lives up to its billing. Don't hesitate...pick your week...and book it!

We are repeat renters of Windward, but have not been able to stay for several years. I am happy to say, the house still does not disappoint. Things I love that have not changed: the amazing views and sunsets, the meticulously clean and comfortable accommodations (especially the bed in the master bedroom), the fully stocked, high-end kitchen, and the amazing view (did I mention that already?).

New things I love: the brand new master bath, the new basement storage closet filled with everything you need for vacation (umbrellas, chairs, coolers, toys), and the individual shower caddies filled with toiletries and sunblock.

Windward manages to be quaint and state-of-the-art at the same time. The sunsets and views of the changing tides are postcard-worthy. And, the house is fully stocked with everything you need for a great vacation. It is truly a unique property - we recommend it without hesitation.

The attention to detail in this home was impressive. Thoughtfully stocked and supplied better than any other vacation home we've experienced. From books to toiletries to kitchen basics and beach necessities, they thought of everything.

Beautiful views and a great relaxing place to get away. This home is lovingly maintained. Wellfleet is full of fun things to do, but does require you drive everywhere. Many sights and activities are just a quick 10 minute drive.

The water is accessible from the home down a beautiful path that feels a bit long for lugging watercraft. It's worth it if you can time the tides correctly and it's not too windy though.

We had a wonderful time in Wellfleet with our 4 grown / young adult children + one significant other. The house was extremely well appointed. As Elisabeth will tell you it has an - "Upside down floor plan/ design". All the bedrooms are at ground/ entry level and were very roomy, especially the master bedroom.

Both bathrooms were beautifully updated with custom built in cabinetry, and all the supplies one would ever need. The kitchen and large open living space are on the 2nd floor to maximize the views of the bay; and the sunsets were spectacular. The kitchen was recently updated with everything you'll need to cook a gourmet meal if so inclined.

Elisabeth thought of everything you'll need for your vacation, from toothpaste and spices to sunscreen and bug-spray, she left no stone unturned.

This home is in South Wellfleet and close to all beaches, with many options available on both the bay and ocean side. The neighborhood is also a great place to stroll around for a casual walk or vigorous run. We will definitely book again when we return to Wellfleet

We've been renting Windward since 2015 and have loved every year. Our vacation this year was just the four of us (2 adults and 2 children) but in years passed we've had grandparents stay with us for a week and friends visit for dinner.

The house has a lovely upstairs where everyone can have dinner and play board games and also plenty of space to read a book on the deck or in the hammock by yourself. It's a lovely house where you relax from the moment you walk in the door - the views are amazing and the house is so well taken care of that there is nothing for you to do but enjoy your vacation!!!

Our stay at Windward was nothing short of amazing. The views are, as advertised, spectacular. We never tired of sitting on the upper deck watching the tide come in and go out. And of course the sunsets were breathtaking.

In designing and furnishing Windward, Elisabeth and Doug have managed to provide vacationers with a setting that is both tasteful and comfortable. There is an overall quaint feel to the house, but at the same time it contains a state of the art kitchen and luxurious bathrooms. My wife and I typically do not sleep well in rental homes. The bed in the Windward master bedroom was so comfortable, however, that we went out and bought our own Tempur-Pedic mattress the day after we returned home.

Elisabeth and Doug have anticipated nearly every need a vacationer could have-Windward truly is a turnkey rental property. Beyond that they are, again as advertised, very available and accommodating. Elisabeth responded promptly to every text I sent to her and had a number of suggestions about things to do at the Cape.

I would definitely recommend Windward to anyone looking to spend a relaxing vacation in a unique, super clean Cape property.

This impressively updated Cape house has a beautiful view on the bay side and is close to many things on the lower Cape. It was perfect for a visit with kids, grandkids and relatives. We aged from 2 to 86. It was well set up for socializing, cooking or heading out to explore.

It is near one of the Audobon sanctuaries for any birders. Everything worked very well and grill and washer/dryer were especially appreciated. There is sun on the deck or shade below depending on time of day.

The owner will check in with you periodically to see if you need anything(information or other) and is most gracious.

Windward was a perfect vacation home for us along with our hypoallergenic Basenjis. They loved it inside and out and made a strong case for never leaving. Now I see they had it right- it was our best escape yet.

The beauty of the house continued to reveal itself through the week. The beauty of the ever changing view with the tides and the light and the sunset both inside and just outside the house was enchanting. We utilized all 4 of the outdoor spaces. The basenjis loved the top deck out in the warm sun feeling the closest they've come to the Sahara. Did I mention the breeze?

We as a family rented out Windward from May 8- May 15, 2021. Starting from our interest in renting until the day we left the rental, Elisabeth was extremely pleasant, and very much in communication with us as far as our needs, and also with her expectations she has for us renters.

Windward appearance looked like it has been very well taking care of. The cleanliness and overall well stocked with just about everything we could need, from pots and pans, to brochures for attractions, to beach chair, to medicine in the the bathroom cabinets. The view is breathtaking with the pond/ marsh in the back yard, from viewing either inside or out! We much enjoyed spending time outside with outdoor seating she has. The kitchen was beautiful, easy access to appliances, and everything in between. The four bedrooms were very sufficient for what we had needed and more.

I would highly recommend this rental, we do plan to rent again!!!

Windward was just a great home for our get a way week in Wellfleet. The house is truly a home made cozy and comfortable by Elisabeth and Doug. There is all one would ever need in the house from all the tools and gadgets in the upgraded kitchen to the comfortable beds and stylish renovated bathrooms. The two days of fog/rain/drizzle made no difference to us as we settled in "at home" reading, relaxing and watching the changing tides, sky and weather from the house.

Best words to describe Windward....cozy, warm, comfortable. Thank you to Elisabeth and Doug for making a lovely place to be.

The 2020 election and Covid prompted my husband and I to seek refuge as well as visit family in the New England area. Our hosts had the most wonderful home, beautiful views and perfect amenities. The proximity of beaches, restaurants and hiking trails were surprising. Wellfleet is welcoming as it is inviting. We highly recommend Windward.

We were so excited about returning to Cape Cod, in particular to Wellfleet. We have rented houses there in past years, but after a stressful spring and summer in NYC with COVID we needed a little escape. As soon as we saw photos of Windward we knew this was where we needed to be, and it did not disappoint us in the least! The house itself is equipped with everything one would need on a vacation. All we needed to bring was ourselves! The house is extremely comfortable and the views from all the windows are spectacular. It's the perfect place to sit back and relax, and the house has so many cozy places to do just that.

There is easy access to Wellfleet proper which is a quaint New England fishing village with a great history. We loved driving around the scenic country-like lanes never getting lost, finding beaches off the beaten path, and exploring the galleries off season was all delightful. Wellfleet is perfectly situated; being close to P-Town, Orleans and the drive south to Chatham is lovely.

The house was just what us city slickers needed to unwind from the stressful past few months, looking out at the bay from the raised terrace of the house and watching the spectacular sunset, taking walks on the beaches, sitting in the comfy lounge by a window in the corner of the room (which I claimed as my own as soon as we walked into the house), and napping while listening to the rain hit the rooftop on the days when the weather did not cooperate was "just what the doctor ordered". It is a tranquil retreat that we would return to in a heartbeat. The owners were gracious, responsive, and invested in wanting to make our stay in their treasured home as comfortable as possible.

Our family gathered at "Windward" in early Fall and it was spectacular. The views, the quiet, the tides and, importantly, the comfort of the house were all outstanding. We've stayed in many rentals and this one had to be at the top of most comfortable (especially the beds) and outfitted. There was, literally, nothing we could have wanted or needed that couldn't be found in the house. The kitchen was supremely stocked with every dish, glass, pot/pan, spice, etc. we could have needed. A true gem.

Upon arriving at Windward and pulling into the shell driveway, my sister and I saw a quintessential Cape Cod home in a beautiful setting overlooking the water. Already we could feel the peace that surrounds this place. But stepping through the front door of this home immediately brings its wonderful character to life!

Up the oriental carpeted stairway to the left is a gourmet kitchen. Top-of-the-line appliances with everything one could possibly need - from every imaginable utensil to small appliances to an array of alphabetized spices stretching across a shelf from one end of the kitchen to the other.

Off the kitchen is the dining room with a huge table for eight. And views. OH THE VIEWS! The website photos cannot do them justice. Every nook and cranny holding books, dried flowers, candles, more books, and a clock that also shows the timing of the high and low tides - immediately putting you in tune with nature here. Watching the tide come in and out and seeing the awe-inspiring sunsets with our wine together each night was heavenly. From the kitchen and dining room, one steps into the living area where comfy chairs and couches stuffed with extra pillows and throws abound. And more VIEWS!

On the first floor of this reverse-living home are four warmly decorated bedrooms. Each one is color coordinated with finishing touches like extra quilts and shams, simple but lovely window coverings, and colorfully decorated wall tiles. I slept in the Master Bedroom and did not close the curtains at night. What a joy to wake up in the morning to once again, see those VIEWS :o)

The renovated bathrooms are amazing. Beautiful fixtures, clean as a whistle (as is the entire home) and big, fluffy towels all ready for each guest.

When we arrived we met Doug, a soft-spoken, charming man who gave us a quick but thorough tour of the home to get us acquainted. We were not able to meet Elisabeth but I texted her several times and she was immediately receptive and gave us great recommendations for hikes and dining. They did not miss a thing at Windward to make it comfortable and enjoyable - it truly is a sanctuary - a peaceful retreat - which we all really need especially now - if only for a short while.

Oh, did I mention the VIEWS?

Thank you Doug and Elisabeth! We can't wait to return!

Winward is a truly beautiful place to spend some time renewing and relaxing. The views are magnificent. The house is immaculately clean and well stocked with anything you might need. The beds are super comfortable. The bathrooms and kitchen are works of art. The owners were available and responsive. Definitely a 5 star rental.

Myself and 3 other family members just spent a fantastic week at Windward and are still raving about it. We have been visiting the outer cape for the last 10 years and we all agree this was by far the best property we have ever stayed at. First thing we noticed was how immaculate and well stocked it was. everything you could ever need in a kitchen ( appliances, cutlery and condiments) is all there. There is practically a CVS in every medicine cabinet and soaps and shampoos are provided as well. Another big plus was the fact that we did not have to bring our own linens( or towels) to make the beds (everyone stated they're beds were super comfortable as well).

My favorite aspect....the view. I could have sat on the deck and looked out over the water all day. The sunsets were just beautiful. Doug and Elisabeth thought of everything to make our visit worry free and were so accommodating from booking to check out. Can't wait to return.

We resided at Windward in Wellfleet for a week this Fall and it was the most relaxing vacation we've ever had. The property has lovely views of the tidal waters from every vantage point, and includes multiple outdoor areas nicely arranged for a quiet read, chat or glass of wine. The home is located a bit away from the highway and was perfectly quiet. All towels and linens are provided, the beautiful kitchen is well-stocked with cookware, glassware, serving pieces, coffee makers, seafood forks, lobster pot & crackers, spices. Many custom architectural features add to the elegant coziness. Master bath has a heated seat in the shower, the best rain shower head, with hair dryer provided. Furniture is curl-up comfortable, along with a veritable library of cookbooks, books about the area and novels. The internet was perfect; we both worked a little during our stay and could depend on it. Laundry is in the basement, which we didn't need but could be useful. We felt right at home.

With COVID you may be happy that many good restaurants (and ice cream) with take-out options are conveniently located both directions from Windward. We enjoyed Wellfleet oysters every night and lobsters, lobster rolls and clam chowder frequently as well. The beaches are beautiful. You can ride your bike to the wonderful Cape Rail Trail from Windward. We drove to Provincetown one day, the beaches there have magnificent dunes. Next time we will go whale watching. You will pass a great ice cream place in Truro - stop!

Windward's owners are gracious and their attention to the details of hospitality unrivaled. The house is a labor of love, constantly improved. They will give you a house tour with helpful information and instructions if you can arrive around 4:00. They are proud of their town and know the residents, history and restaurants. Brochures are mailed in advance so you can plan your outings. You really don't need to pack much at all - just go!

This home is well cared for, clean, comfortable and nicely decorated. Windward was a perfect place for two couples and occasional overnight guests. Enough room to entertain and the bedrooms were like a B&B. Comfortable, spacious and quiet as they are on a separate floor from the living area. Best of all are the sunsets, every evening of our stay we made sure we were back at Windward to watch the amazing sunsets. We would definitely stay again!

Our experience at Windward was tremendous. The views were breathtaking, especially at sunset. Easy access to beaches, kettle ponds, and downtown Wellfleet. Amenities abound at Windward. The homeowners ensure that your stay is worry free. They meet you upon arrival to acquaint you with the property, its features, and local points of interest. Our family of four with two small found the home welcoming, well apportioned, and meticulous. There is no hyperbole in any of the description of this wonderful home.

We'll be back in 2021!

We stayed at Windward during the last week of July 2020. We were very impressed by both the stunning setting and sunsets, and by the attention to detail that the owners have placed in every aspect of the property. I am guessing that most guests consider making an offer to purchase the property before they leave.

Our family just stayed at Windward for three weeks, July 4 to July 25, 2020, It was the most relaxing vacation you can imagine, a complete escape in these crazy times.

First, can we talk about the view!?! No matter the weather or the time of day, it was a beautiful soul satisfying experience to take in the enormous panorama, from the marsh over the bay toward the sea, where huge sand dunes shined in the distance. Sunsets are out of this world. I wish I could post photos.

The up-close view of the monarch butterflies stopping to feed on the butterfly weed was equally enjoyable. As were all the lovely walks we took from the house down small paths and sandy byways to the shore or just around the neighborhood.

Doug and Elisabeth were perfect hosts; friendly, discreet yet ready to assist if needed. The house is exactly as advertised, I mean EXACTLY! a rarity these days. It's exceedingly clean, allergy friendly and well laid out to accommodate groups of up to 8 people.

The house's upside down design, with kitchen and living areas on top, allows everyone to enjoy the view. Never been in a rental with such a well-stocked kitchen, though I wish there were sharper knives. The wood beams and walls and custom art create a warm atmosphere. People would congregate for meals and board games or use the varied spaces upstairs to enjoy watching tv, reading on the chaise lounge, taking in the view from the deck or working remotely on a laptop at the dining room table.

The bedrooms are equally well-appointed as are the bathrooms. I enjoyed a lavender scented bath in the claw foot tub. There are beautiful views from the master bedroom and the other rear bedroom. The ones in front, which are slightly smaller, look out into the trees and feature the same amazingly comfortable beds. To me, this was key!

Even the basement is nice, spotless with laundry and every kind of beach item you could possibly require —- sand toys, chairs, bogie boards, coolers, noodles, etc. We also made great use of the (two!) outdoor showers and all the lovely outdoor seating scattered around the property.

My criticisms are so small as to be laughable. There are too many pillows and the blankets covering the couches got messed up easily. See what I mean?

Elisabeth does an amazing job of providing you with information about the area. Getting a beach sticker was a seamless process. I cannot rave enough about swimming in the crystal clear glacial kettle ponds scattered around Wellfleet! It's truly heavenly to take a noodle and swim out to the middle after a long day at the beach or early in the morning when no one's around. And then there's the beaches, all worth a visit. Best moment: standing atop the dunes at Marconi and watching a whale breaching repeatedly just offshore.

There's so much else to do and see. We went out to Ptown, drove around looking at beautiful old houses and gardens, then out to Race Point. Another day we made a scenic drive to Chatham, had lunch at the Chatham Bars Inn beach restaurant. We loved the boardwalks and walk out over the sandbars at the nearby Audubon Sanctuary. Played golf twice, once at the country's oldest links course in Truro, the other time in Wellfleet. Both by the sea providing breezes and views throughout our rounds.

Always lovely to visit the shops and galleries in downtown Wellfleet, have a meal at the Pearl down by the harbor or pick up seafood at Mac's or one of the other town fish markets. I love the Willow Bakery on Route 6, organic and scrumptious! Many other good restaurants nearby, including PB bistro and boulangerie and Van Rensaleer's.

In short, this is a can't miss choice for a vacation rental home, a place where you can relax and have a truly memorable Cape Cod escape.

We have been coming to Windward for six summers now and love every last detail about the home and the property. The view alone would be enough to have us coming back year after year but the house is so well appointed and clean that we always know what it will look like when we arrive and we are instantly "at home". The kitchen is well appointed and so well organized it makes cooking a joy on vacation. The bedrooms have all of the details that make it comfortable from the moment you unpack and the air conditioning is an added bonus for those hot stretches on the Cape to escape the heat. It is a perfect home for your family and/or extended family - enough space for everyone to join together when they want and escape when they need a break!

Our stay at Windward exceeded our expectations in every way. The house is impeccably cleaned and the water views throughout the day, especially during sunset, are absolutely stunning. Every amenity you might need for a Cape Cod vacation is available, including lots of beach toys (for all ages!), floats, chairs, coolers, and umbrellas, etc. All the beach items and high quality linens made our vacation very comfortable and packing for our trip much easier.

The layout of the house is fabulous for relaxing, taking in the water views, and cooking either in the fully appointed kitchen or grilling on the deck. The outdoor shower has enough privacy for bathing or to use as a quick after beach rinse. We found the house to be beautiful, comfortable, incredibly clean and a very relaxing place to vacation.

The owners go above and beyond to make you feel at home and welcome in this very special Cape Cod vacation rental. We highly recommend this home!

Our days were bracketed by the tides, making an ever-changing view. Wine at sunset, then a dinner cooked in the fully equipped kitchen, often fresh fish from the pier. We were 6 adults, all delving into books, pleased that there were plenty of comfy places to curl up and read. The bathrooms and laundry had every sort of toiletries you could possibly need, and there was a virtual pharmacy of OTC drugs. The outdoor shower nicely supplemented the 2 and 1/2 bathrooms. There was a complete supply of beach chairs, umbrellas, etc., and Elizabeth made sure we had all we needed. Besides the beautiful beaches we enjoyed strolling through Wellfleet's art galleries and eating at the local restaurants. All in all, it was blissful.

We have stayed at Windward twice and the house is wonderful. As you can see from the reviews this is a well equipped rental. Typically we bring tons of supplies for our annual Cape vacation. Not needed for this property. Pretty much everything you need other than clothes is provided by the owner. The kitchen is terrific. All you need is food. Every imaginable appliance, utensil, pot or pan can be found in the well stocked cabinets. Same for the bathrooms; everything you might need is there from soap and shampoo to first aid grooming. The medical supplies came in handy this year when I had an injury at the beach. This is a lovely home in a quiet part of Wellfleet. If you happen to need something the owner is very responsive.

We have been coming to this wonderful home for at least four years now and we look forward to our week every year!! The home is well appointed and always very clean! The space is big enough for my family (two adults, two children) as well as my parents and my in-laws. The sunsets out on the porch are outstanding - truly can't be beat. Windward is a fantastic way to enjoy Welfleet!!!

We spent a week at Windward with another family who we have vacationed with for more than a decade. I can honestly say we have never had a more seamless and enjoyable week. Everything previously mentioned about the level of accommodation and organization is true! The sunsets are spectacular!! We brought our kayaks and paddled around the creek and saw turtles and egrets and pipers (oh my!). As we approach fall, I can only imagine how spectacular the view with the fall colors would be. We will definitely be back next year!

Windward is amazing. It is beautiful and amazingly well stocked and organized. All of the beach items you think you need and that you don't know you need are there to use. My family and I had a fantastic time. I highly recommend this house to anyone.

Hello. My family and spent yet another beautiful vacation at Windward. It was our third visit. The good (and bad) news is that we cannot return next Summer due to our family having many happy events - graduations and a wedding and our timing is a little uncertain as of now. But, let me tell you, we have not had our last visit to Windward. The home is completely turnkey when you arrive - no lugging sheets or towels or renting them. When you arrive EVERYTHING is there and done. Beds are made....a/c is on......all you have to do is unpack and enjoy a libation or beverage straight away! Your vacation starts immediately.

The home has much character and is exceptionally warm and inviting. Every detail has been thought of to make your stay wonderful and the home is IMMACULATE!!!!!!! Truly. This is a dream vacation home, with many unique elements throughout - including a beautiful outside shower area (not typical). Also, one of our favorite aspects is that you can all be together as a family easily but yet there are many places to lounge and relax if you are looking for a bit of solitude. It has everything, central AC, immaculate, a beautiful deck, the VIEWS (which never disappoint no matter what time of day it is or cycle in the tide), 4 beautiful bedrooms....beach chairs, coolers and the like (no lugging anything to this vacation!). And the owner, Elisabeth, is lovely. She is very kind and responsive to any need or small problem you may have during your stay.

It is also in a great location - very close to the bike trail and Marconi Beach and just a short drive to the center of Wellfleet and about 20 minutes by car to Provincetown. Absolutely book this beautiful home if you have the chance - you will NOT be disappointed and I venture to guess you will also be returning once you have spent time there! Bon Vacance! And thank you Elisabeth - we will most definitely return.

This was our first vacation in Wellfleet and at Windward, and we will be back next year. You can read the other reviews about how well appointed and immaculate this property is. It's all true. This is not a typical rental property. More like staying at a friend's house. Everything you need is in the house from shampoo, detergent and bug spray to beach chairs, blankets and towels. Normally we fill half our car with items for the kitchen, beach and linens. None of those things are needed at Windward. All you really need is personal items and clothes. Before we arrived we asked Elisabeth about outdoor adult toys (corn hole, bocce., etc.). She didn't have those but when we arrived she had bought them. When we had small issues (tripped a circuit breaker) she sent help immediately. We had a wonderful experience at this house and our kids and friends thought it was terrific. We enjoyed being in Wellfleet, an easy commute to beautiful beaches, Provincetown and Chatham. I'd recommend this property without hesitation.

This is our fourth year returning to Windward, and as always Elisabeth does an exceptional job getting the house ready to make sure our stay is perfect. The house is always so clean, the beds beautifully made and even the classical music station on when you arrive!! The house has everything you need for your stay and then some - the kitchen is great to work in and she has all of the cookware to help (you never scramble to find something - she has it all) and plenty of other home essentials for a great vacation - puzzles, board games, books and boogie boards for the beach. It is a wonderful home and fits for all of us - parents, grandparents and kids alike!!! Thanks, Elisabeth!

5 stars. Property is as described. During 3 week stay there were as many as 6 adults and 4 children in the party. The property easily accommodated all. Not necessarily a property for active kids under 10 unless one plans to hit the beaches every day as the grounds around the property are protected. The owner might appear to be rather controlling as she sends out a 16 page history of the house , recent renovations, and dos and don'ts, but this is not the case. She is understandably proud of the house and the Cape Cod atmosphere one enjoys within it. She is very discrete during one's stay. One improvement would include an outdoor light on the second floor patio deck.

Windward has everything set up for anything you could possibly want to do. There are beach chairs in several varieties, umbrellas (with corkscrew), and the best beach blankets ever. (We’ve already ordered one.) The house is very close to our favorite kettle pond. We enjoyed running out to the ponds and beaches while the grandparents enjoyed sticking close to the house.

The house is immaculate. This is NOT a spidery Cape Cod by the beach (although we like those too). This house is well appointed. The kitchen is spectacular to cook in, and the views from the deck are stunning at sunset.

We had family come in from all over the country, and Windward accommodated us perfectly. If you’re looking for a turnkey house, Windward is the place.

Home away from Home but better - you’re in Wellfleet! My family and I just returned from our second stay at Windward, and we were once again delighted by this home! This home is very unique, beautiful and is in a gorgeous location as you can see in the photos. What you cannot see in the photos is the ease in which this home envelopes its occupants. There are rooms to gather and plenty of spaces for privacy and relaxing. Our favorite spot is the deck off the kitchen with the spectacular views; but, the seating areas underneath the deck and by the hammock (the hammock!) provide quiet spots to read, rest or have a private conversation.

From the moment of entry one is keenly aware that this is a home that is cherished and was built with love, great care and attention to detail decoratively and otherwise. Elisabeth is a lovely woman and has tended to every detail - and is also readily available should anything come up during your stay. Upon arrival, you will find a pristine home that has everything you may need and is very organized. We have been coming to the Cape every year for at least 25 years, and this is by far our favorite house. You only need bring your personal belongings. Elisabeth provides all linens (the very comfortable beds are made up prior to your arrival), beach towels, beach chairs - anything you might need at all is at this house and is in good working order and easy to find. The view, the linens, the air conditioning and the uniqueness of this very “Capey” home make this our favorite home of all time in Wellfleet and we plan on returning as long as Elisabeth will have us! Do not have any reservations in renting this home - it truly provides a sublime vacation.

We had stayed at this place in 2008 and remembered it as a nice place, so we scheduled it for a month long stay. The house was beyond phenominal this time! The new air conditioning was a plus on the day of our arrival as it was very warm and the heat was welcome also during our stay. The upgraded baths are so nice, and the outdoor shower was great especially well done and enjoyable.

I am a clean freak and always travel with all kinds of cleaning supplies and my own set of linens, pillows and mattress cover for my bed. Which is TOTALLY unnecessary at Windward!!

The house was spotless, the bed linens were absolutely luxurious with lovely sleeping pillows on all the beds. Bed covers and blankets were also clean and high quality. The baths all had high end bath towels, hand towels and wash cloths.

The owner had upgraded the kitchen which included a Wolf gas cook top, stainless steel appliances, double ovens and every type of cooking pots and pans. baking items and cooking utensils you would have in your own home. Preparing meals was a dream, and the home included a lovey collection of spices to use. No need to rush out to the store on arrival because all the basics were there! The place even had placemats and cloth napkins and plenty of dishes to serve a large family or create a romantic setting for two.

Every room in the home has special places to curl up and read or nap with beautiful views of the water and marsh. The art work in the home is lovely, the additional supply of books to read great, and it you want a truly relaxing vacation with that "Ritz Carlton" touch and feel, this is the place for you!

As a group of old friends from high school, we love spending time together but have had a hard time finding the perfect house to rent. This is the first time in our several years of going to the Cape together where we wanted to rent the same house again; thank you very much for providing such a lovely, welcoming, well-appointed and comfortable home!

Windward is a lovely home with an amazing water view! If you're interested in riding bikes on the rail trail, you'll be pleased that you can ride through the quiet neighborhood and easily get on the trail. Wellfleet beaches are amazing, and the homeowner provides all the necessary beach gear - a huge bonus! The interior of the house is beautifully decorated with lots of comfy seating, and the kitchen is fully stocked with everything you need plus some! We had a wonderful week sitting on the deck enjoying the beautiful view, visiting all the great beaches, bike riding and playing games around the big dining room table! If you're looking for a great family home for your teenagers, Windward is for you!

Our family-and-friends group of six adults enjoyed a fabulous September week at Windward for the second year on a row. The property is represented well by the photos, but it is much, much better being there. Perched over the bay as it is, the view is not only stunning but also endlessly fascinating and beautiful as the tides go in and out, constantly changing. We love the way we can walk right from the house as far as we wish along the bay. The house itself is very livable, with plenty of room to hang out together, cook in the gourmet kitchen, dine, or be alone in one of the living rooms or on one of the decks. You can tell that the owner, Elizabeth, truly loves Windward, and it is evident that she is attentive to making sure everything is in good order. We love being at Windward and are hoping to make it three years in a row. This year we appreciated the beauty and functionality of Windward even more than the first time. Those sunsets grow on you! Top notch getaway home!

Our one week stay at Windswept was awesome! The owner really takes pride in providing all that is needed for a perfect vacation. The pictures do not do it justice! From the gas grill, to the gas stove, flat screen TVs, super modern microwave, and oven, to the small things like poison ivy remedy, (which my Dad got while golfing) there was nothing but food and drinks that we needed to bring. I looked for countless hours to find the perfect home for all my family's needs and I found one. I needed an exceptionally clean, and mold/mildew free place for one of my guests due to allergies/asthma. Also enough bathrooms to accommodate all of the guests.

The house was exceptionally clean, and the easy to use AC on both floors helped a great deal with the 95 degree muggy weather day we had on our week! It was also a great location for all of our day trips, from Provincetown to Sandwich. All of my guests, as was I, were pleasantly surprised of the all extras that were included to make our vacation special. On top of having a fully equipped house from beach towels, to umbrellas, to any kind of spice, cooking pans, glasses, plates, blenders, you need, nothing compared to having such a spectacular view at any time of day, but especially sunset. I recommend this house to anyone who is interested in a quiet, worry-free vacation.