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Wellfleet Vacation Rental home in Cape Cod MA, ....2 minute walk to edge of water at Windswept | ID 3600
4 BR
2 ½ baths
Sleeps 8
Beds: 2 kings, 1 double, 4 twins, pack and plays ( 2)
Beach: ....2 minute walk to edge of water at Windswept
OWNER SPECIAL: $500.00 deduction on each of last two weeks in September!!!!!
Daily
Weekly
Monthly
Summer 2025
 
Off-season 2025/26
 
Summer 2026
 
Summer 2025
$7,500
Off-season 2025/26
$3,000 - $7,000
Summer 2026
$6,500 - $7,500
Summer 2025
 
Off-season 2025/26
 
Summer 2026
 
State and local taxes of 14.45% will apply
Listed by Windward
Active
18+ years
Property ID 3600
3
Description

Description

With amazing water views (some of best on Cape) this wonderfully comfortable house is lovingly furnished (Persian rugs, antiques, authentic cottage furniture, custom made coaches, chairs, day bed,and stuffed rocking chairs) and as such has a unique ambiance. Unlike the typically constructed house, Windward is a post and beam structure (all wood inside and out) that is also an incredibly bright/light home. In addition the homeowners wanted a house that was a quintessential cape cod house from the street side view but wanted much glass on the water side of the house to to take advantage of the amazing views. It has an open floor plan (but also with niches and crannies), 15 ft. cathedral ceilings and enormous numbers of 6 ft by 6 ft windows showcase the amazing panoramic water views and spectacular sunsets. The living area is essentially a huge screened porch (if the gliders are open and the A/C off).

This house provides it all. Windward offers you a ''turnkey'' home to start your summer vacation. You need only bring yourself and your own personal items as Windward is totally set up for you to start your vacation from the moment you arrive. No making beds,lugging beach gear,or anything else for that matter. Only SHED LESS dogs are permitted unless specifically agreed between homeowner and vacationer.

At high tide, you look right ...out at a mesmerizing view of sailboats, skiers, and other watercraft... whether the sea is calm or in a there is ''chop''. At low tide, you will be struck by the plethora of amazing flocks of water foul (not to mention more than a few oyster gatherers). Windswept's view is looking out toward Great Island.

Windward is close to many of Wellfeet's ocean, bay, and pond beaches, including its own. There are more bay , ocean, and pond beaches in Wellfleet nearby...more than any other town on the cape.Accessing any beach is easy because Wellfleet is narrowest town on cape.
for example, you can access a bay, ocean, or pond beach all within 5 minutes from one another.

Windward is within biking distance of the entrance to the Cape Cod Bike Trail. You can ride directly to trail from house without using a car. The Wellfleet Bay Sanctuary ( largest Audubon Society in MA. . Every day and evening you will have an abundance of activities from which to choose. There are the Shakespeare performances, nightly concerts, poetry readings, historical lectures, book signings, outdoor movies and inside cinema, a large combination of both cuisine eateries and family restaurant. All watercraft is available to rent for your use individually and there are many chartered options ( sail, fishing, sightseeing) as well.There are two amazing theaters in town that produce some of the most innovative and spellbinding performances all with professional actors. Every night, there are multiple professional offering making it difficult to choose which one to choose. Also, laying low at Windward watching the sunset from the deck is often a popular choice after spending all day at the beaches.

The Windwardt home itself has a very large open living space (LR, DR, and kitchen.) It has multiple clusters of seating areas so groups with differing agendas may enjoy an assortment of activities.... while remaining together on one floor. All floors are covered with authentic Oriental Persian rugs or hand made area rugs.

In the sitting/dining room there is a huge (4 seater) coach, a day bed, Morris chair, platform rocker, and Bose music system. This room also has a claw and ball antique table that can seat from 6 to 14 people depending on your needs. Unless watching TV or needing different rooms for different clusters of family members, this is ''everyone's'' favorite living space.

The LR also has many gliders and has equally fabulous water views. It has a seating arrangement that has 2 couches, a large matching stuffed chair and a rocking chair. This room has the upstairs TV with an extensive cable subscription.

The new (2012) gourmet kitchen has hand made wooden counter tops, custom built shaker style cabinets made of white ash, a huge island with recycle bins, new commercial grade stainless steel appliances (gas stove), and a lovely new slate floor. ( The woodworker had this kitchen featured in Fine Home Building Magazine. The amazing lighting artwork/ fixtures in the kitchen is the signature piece of the kitchen. The kitchen is provisioned for even the most sophisticated gourmet cook (between the pots and pans, baking dishes, every gadget imaginable, and more spices than you could imagine.

In both primary living spaces, you will feel like you are sitting right ''on top'' of the bay.

In 2013 we added a ''one of a kind '' double room outdoor enclosed shower with a dressing suite as well. The new outdoor shower has a private entrance from the master bedroom. There is a second outdoor shower adjacent to the back door.

The first floor has four bedrooms. The MB has a king size bed with a Temper-Pedic mattress and three 6 foot by 6 foot glider windows showcasing more fabulous water views. Also, the MB has its own sitting area, cable TV, a second Bose Music System, and its own master bath. The other three bedrooms all have access to the main bath off the center hall. One bedroom can be set up with a king size bed or two twin beds, another bedroom has a set of twin beds and the fourth bedroom has a double bed. All beds (other than MB have either custom made mattresses which are usually comfortably and always commented on.The latter was necessary because much of the furniture is authentic refinished voltage furniture or 1800 antiques.

There are two bathrooms on the floor with the bedrooms. The main bathroom was totally gutted and redone with the latest and most upscale products in 2015.This bathroom has a huge standing shower with glass on tow sides and abuts a huge tub ( both in height and length. Where there isn't hand plained wooden ( copied from master wood builders in the 1800 century ( all tongue and groove), the walls are white subway tiles.

The master bedroom private bath was just completed this summer ( also gutted at outset) It has a built in seat at end of shower that you can choose to heat. It also has a ceiling radiant heater in ceiling and an incredible amount of custom built cabinets. Many are built into walls so bathroom still feels airy and the glass door on shower is a practical and aesthetic choice that further enhances the MB bath. The till in shower, and floor is made of stone.

At Windward, the vacationer will have access to umpteen non fiction books about Wellfleet and Cape Cod. There are always plenty of top ten recent fictional books and fictional books either written by local authors and/or set in local cape cod settings.They are located next to a daybed that ask has magnificent views of the bay.

Our goal is to provide a unique home to Cape Cod vacationers. We are committed to insuring that Windswept provides a feeling of casual luxury, a home with exceptional water views, and a home that is exceedingly welcoming upon arrival. The house has a team of cleaning people including the owners who spend at least 24 hours between departing and arriving guests, cleaning/readying the house for our incoming guests. You, the vacationer, need only begin your relaxing, special and comfortable vacation. Every bed is made up with 600+ percale cotton sheets. Every room has been cleaned from top to bottom. Windward provides beach towels, bathroom towels, beach chairs, beach umbrellas, boogie boards, and other items upon request. It is our hope and wish that, with the fabulous breezes, the comfortable and luxurious feel of the house, and the majestic views, you, our guest, will feel immediately upon arrival. ACCEPT NON SHEDDING DOGS ONLY except when mutually agreed to permit otherwise.

There are 4 outdoor seating areas with tables, chaise lounges. One is in the pines in front of Windward where it is cool but not so breezy. One is specifically designed for use by those that are the renters in the MB. Another is one the second floor and while it is directly exposed to sun, the breezes off the water make it a favorite outdoor space. Those that want the same view and comfort can choose a patio directly below the deck.
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Location

Location - Wellfleet

Nearest beach: ....2 minute walk to edge of water at Windswept

41.906602 -69.995488 0
Photos

Photos

Pricing & Availability

Pricing & Availability

1
OWNER SPECIAL:
$500.00 deduction on each of last two weeks in September!!!!!
Minimum Stay Requirements:
  • Summer 2025
    7 nights
  • Off-season 2025/26
    7 nights
  • Summer 2026
    7 nights
Available
Unavailable
Unknown

Calendar Last Updated: August 21, 2025

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Additional availability info: Usually, Windward is booked by the previous winter holidays, preceding the vacation year,. This is a Saturday to Saturday vacation rental.

Payment Methods: PayPal (3.49%); and personal checks

Other Fees:

Additional Pricing Info: Windward is a 'turnkey' vacation home. No need to bring anything but personal items and provisions. State and local taxes of 14.45% will apply

Amenities

Amenities

  • On a salt water beach On a salt water beach

  • Central air Central air

  • Outdoor shower Outdoor shower

  • Washer&dryer Washer&dryer

  • Pets considered Pets considered

  • Internet Internet

  • Linens provided Linens provided

  • Deck, porch or patio Deck, porch or patio

  • BBQ-grill BBQ-grill

  • TV TV

  • Cable/satellite TV Cable/satellite TV

  • Coffee maker Coffee maker



    Green Amenities

    3
    • LED lighting LED lighting

    • ENERGY STAR appliances ENERGY STAR appliances

    • Reusable grocery totes Reusable grocery totes

    About our green amenities: Also, there is a very (made easy) specific recyclable area built inside a large pull out cabinet size drawer. This contains a tall basket for each: glass, tins and plastic, and cardboard and paper. This allows vacationers to sort recyclables with ease.

    Reviews

    Guest Reviews

    5.0 122 reviews
    Have you stayed here? Write a review
    Danielle D.
    Westford, MA
    2 reviews
    Beautifully Maintained, Fully Stocked, and Close to Nature
    August 2025

    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.
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    Date of stay: July 2025
    Ann M.
    Cranston, RI
    2 reviews
    3years on WeNeedaVacation
    Wonderful Windward
    August 2025

    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.
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    Date of stay: July 2025
    Jenifer S.
    2 reviews
    8years on WeNeedaVacation
    Perfect Wellfleet Getaway with Stunning Water Views and Exceptional Hosts
    August 2025

    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. show more show less

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    Date of stay: July 2025
    Sarah F.
    Denver, CO
    1 review
    Great House
    July 2025

    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!

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    Date of stay: July 2025
    Elizabeth H.
    Washington, DC
    2 reviews
    3years on WeNeedaVacation
    Another Perfect Stay at Windward
    July 2025

    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.
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    Date of stay: June 2025
    CAROL H.
    Sherborn, MA
    2 reviews
    7years on WeNeedaVacation
    What a wonderful home!
    July 2025

    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!! show more show less

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    Date of stay: June 2025
    Jeffrey D.
    Salem, NH
    1 review
    1month on WeNeedaVacation
    A wonderful weeks stay at Windward South Wellfleet Ma
    June 2025

    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!
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    Date of stay: June 2025
    Robin S.
    Knoxville, TN
    1 review
    2month on WeNeedaVacation
    Well appointed
    May 2025

    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. show more show less

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    Date of stay: May 2025
    Kristin H.
    Sudbury, MA
    4 reviews
    17years on WeNeedaVacation
    Another Glorious Stay
    October 2024

    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! show more show less

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    Date of stay: August 2024
    Kathryn
    Salt Lake City, UT
    1 review
    11month on WeNeedaVacation
    Glorious Family vacation in Wellfleet!
    September 2024

    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. show more show less

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    Date of stay: August 2024
    About

    About Windward

    Member since:
    9/17/2001
    Reviews:
    122 reviews
    Response Time:
    Within a day
    Response Rate:
    100%
    I have been renting Windward through WeNeedaVacation for 12 years. Before this rental site was launched, I was fearful of renting Windward because I wanted to have a direct connection with the vacationer to be sure Windward was the most well suited house for the needs of you, the vacationers. It is very important to me that vacationers experience at Windward exceeds their expectations.

    I keep the house unusually well maintained both inside and out. Every year, I spend a huge amount and expense on making Windward even more special than it was year before. I feel this is a never ending adventure to create new concepts for Windward's interior and exterior. This is a passion for me that translates into an amazing plus for vacationers. Returning vacationers are always equally anticipating the new completed projects completed each year.

    What is special about this property?
    Windward's greatest asset is the compliation of many facets. !) its locations with amazing views and sunsets, 2) It is a non rental location wherein it is quiet and tranquil 3) It has amazing breezes ( if neither of 2 central A/C units are utilized 4) the post and beam construction itself and wide planking which came from wood centuries of years ago 5) the house's main living space lay out which lends itself to having people being able to do many different activities without being 'cut of'' in different rooms 5) all the custom furniture and original refinished cottage furniture and antiques which create a special ambiance. 5) its quintessential cape cod feel coupled with all new state of the art rooms like its kitchen, overhanging deck, bathrooms 6) the meticulous care provided to this house on an annual basis. 7) the 24 cleaning spent on readying the house between vacationers. 8) the attention to detail in so much that you, the vacationer can arrive without bringing the typical beach gear or linens and enjoy that the owner has provided the work to completely ready the house for your arrival.

    What is special about your town?
    Wellfleet is situated on the narrowest width of Cape Cod. This means that it ( in some situations ) only a bike ride away from the huge and rolling waves of the Atlantic Ocean beaches to the more calm and warmer waters of beaches on the bayside. Also, Wellfleet is known also for the abundance of Kettle ( freshwater) ponds which also have beaches to which you have access.

    Wellfleet actually has a quintessential town center that presents very much as it did a century ago. Most of the same homes and other structures are in tact and lovingly restored to show as they did at the formation of the town. There is a local market ( with almost anything you could need), ice cream shoppe, liquor store, pharmacy just before entering town, bakeries, restaurants, many gift and boutique shoppes.

    Wellfleet has an an unusual number of spaces wherein activities are planned almost all the time 1) Preservation Hall, WHAT, Wellfleet Harbor Actor's Theater, Audubon sanctuary, Cape Cod 30 plus mile bike ( Rail Trail), ) Art Gallery town, amazing
    recreation facilities for children,

    Wellfleet the town that is the exact middle town of outer cape. Truro and Wellfleet are in one direction and Eastham and Orleans are in other.

    Windward is in the center of it all ( albeit tucked in off on a sand road). One can walk, bike to all three types of beaches ((ocean, bay, pond) , bike to Rail Trail and Audubon sanctuary, theaters, restaurants, and is only a couple of miles from the town center.







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