Waterfront Estate with Private Beach & Brand New Pool
Orleans Vacation Rental - ID 19054

My family, mother, children, grandchildren and great grandchildren gathered to celebrate the life of my father. 50 years ago we would walk below this bluff to go clamming. We would sail and waterski in the bay with this classic home looking down over us. It was my fathers happy place. Both indoors and out, this is the quintessential Cape Cod experience. The spaces inside and around the property provide for large gatherings, intimate conversations and private reflection.
You can sense the history of gatherings taking place over the past decades. If you can't enjoy this home, property and surrounding views then you simply can't enjoy all the Cape has to offer. If it's the people/family gathering to celebrate living a good life, past, present and future, this is the perfect place!

What a gorgeous setting for a wedding! The grounds of this estate, with the views of Pleasant Bay, the beautifully maintained lawn along with the comfort of a spacious and comfortable large home made this the perfect place to hold our daughter's wedding. Our guests could not stop commenting on the beauty of the venue which made the whole weekend magical. Just as important, Ginger and Ken the owners, could not have been nicer or more accommodating. They were responsive, clear and easy to communicate with every step of the way. Our daughter and new husband stayed on to enjoy a short mini-moon and loved their stay, enjoying the well maintained pool and the waterfront.

We were fortunate to host our wedding at Winslow Estate in May 2022. Ginger and Ken were extremely helpful and always available to answer our questions along the way. We thoroughly enjoyed soaking in the week with family and friends. The venue was as stunning and picturesque as advertised, and we look forward to returning for anniversaries in the future! We absolutely recommend the Winslow Estate.

The Winslow Estate is the perfect place to have a wedding. The Estate itself is gorgeous – the house is beautiful and spacious – totally cape classic inside, the backyard is huge, and the water view is unbeatable. The pool and grill area are also a fantastic touch.

You have the flexibility to really customize the wedding to be whatever you want it to be. Renting the entire estate for a week allowed us and our bridal party to arrive several days early and prepare for the Saturday wedding. After the wedding, we were able to simply relax and enjoy the house and the views for several days.

Truly you will never be able to find another wedding venue on Cape Cod that has a backyard home vibe right on the water, that allows you to create your dream wedding with your favorite vendors. So many of our guests came up to us, absolutely gushing about how perfect the wedding venue was.

Ginger and Ken are absolutely wonderful to work with – they are organized, kind, and great communicators. They were flexible and worked with us with extraordinary patience as we postponed our wedding multiple times due to the pandemic. They also emailed me several times throughout the pandemic, simply asking how we were doing and we really felt cared for during the entire planning process. They really made the Winslow Estate feel like a home while we were there, and we couldn't have had a better experience. They were also very helpful on the wedding day, helping our guests with parking and guiding them to the afterparty at the end.

We loved every second that we were at the estate and already miss being there. My husband and I are already talking about renting the house again.

We hosted our daughter's wedding in this beautiful home that sits on a piece of property that is private and wrapped by the bay. The view is spectacular.

The house itself is "Old Cape Cod" with lots of charm. There is a huge living room where our group liked to gather in the evening. There are two kitchens, a beautiful screened porch (perfect for bridal party hair and makeup), several outdoor patios, and a gorgeous new swimming pool. The bathrooms have all been updated. The many bedrooms were ideal for the families and bridesmaids, while the groomsmen stayed in the nearby Bay House. This made it easy and fun for the bride and groom. (There is a small resort 10 minutes down the road for additional guests.)

The property is set up to accommodate weddings. There is room for a tent, lots of parking, plenty of electricity, and indoor bathrooms to use. The owners, Ginger and Ken, were extraordinarily in helping us. They helped with vendor ideas and helped us pull it together on the actual wedding day. They are nearby when needed but never in your way. Ken has a cool little golf cart he uses. If needed he will transport guests with mobility issues. Our bride had a fun ride down to the deck by the water and back for her "first look" with her groom.

All in all we had a magical wedding week at the Gentle Heritage. The home is both large and comfortable. The location is second to none. There is plenty to do right on the property but it is also close to Chatham and Orleans. The new pool was the icing on the cake in the days after our wedding. It is the perfect spot for weddings or gatherings of any kind.

I married my sweetheart at Gentle Heritage this past Spring, and we were both blown away. Mother nature pitched in with a warm day w/ wall-to-wall sunshine, but the venue itself was simply spectacular. The several days we spent over the wedding weekend were storybook.

The house and property itself has a character that is uniquely special, a blend of charm from of what I characterize as old Cape, with the modern luxury that pushes the experience over the top (the new pool is a masterpiece). My wife and I both won't stop raving to everybody and anybody. We wish we could re-live it all over again.

Ginger and Ken were outstanding hosts that only added to our stay. They are gracious and very passionate about the property and its rich history. And hilarious too! They helped us plan around different wedding vendors for our big weekend, and all of their recommendations hit it out of the park.

Can't say enough great things about the property. I close my eyes and picture the stunning view from the lawn. Anybody that wants a life-altering experience (whether you are getting married or just need a vaca), we recommend Gentle Heritage.

Pete C
Boston

We were fortunate enough to hold our wedding at the Winslow Estate and I must say that the pictures do not do it justice! Ken and Ginger were beyond amazing hosts and we couldn't be happier with our stay. The home is absolutely beautiful, comes with all the amenities needed for hosting a large gathering, and the property is second to none. There's a reason this home is in such high demand and I cannot recommend it enough!

We enjoyed every minute at this beautiful property! All of the vendors that Ginger and Ken suggested were perfect, especially David at the linen company! We greatly enjoyed hosting 7 couples here to celebrate my 40th birthday. The estate was stunning with amazing views and such a unique Cape Cod experience! The location of the home is ideal for visiting so much of the Cape as well! We would love to come back again and bring our children during warmer months! Thank you to Ken and Ginger for being fantastic hosts and sharing this lovely home with us!

Our family has vacationed on Cape Cod for 50+ years so finding "the perfect spot" on Cape Cod for our daughter's wedding was beyond our wildest of dreams.

Danielle and Tom spotted Gentle Heritage from across the bay when we were touring another "wedding venue". Danielle and Tom knew that they didn't want to be rushed with a 4-5 hour window during which to celebrate their Wedding Day. From our first visit to Ginger and Ken's Winslow Estate (Gentle Heritage), we knew this was the location of locations. We had 12 guests stay with us in Gentle Heritage (the groom's family rented the Bay House below) for the entire week (Wed. - Wed.) and everyone agreed that everything was just perfect. From the location on Pleasant Bay to the sprawling yard and beach below, the views were spectacular. Well apportioned with everything we could possibly need to entertain for the week- clean living areas, updated bathrooms throughout, comfortable bedrooms, a gorgeous heated pool and patio area completed with ample seating for all guests, and spectacular views from every location.

Our pre-COVID planned 175 person wedding was scaled back by the Governor of Mass. (with a 50 person outdoor max. limit for COVID-19 infection mitigation) and while the property can easily accommodate a much larger outdoor event, the celebration was just perfect at 50 guests. Ken and Ginger did everything right from the first time we spoke with them in the Fall of 2018 to the immediate return of our security deposit upon seeing the condition we left the property in. They made themselves available to us throughout but were unobtrusive.

While the Saturday afternoon/evening was the main event, complete with "jaw dropping" superlatives relating directly to the ambiance of Gentle Heritage and majestic views of Pleasant Bay from the guests, our family that spent the week with us at Ginger & Ken's property relished the family meals enjoyed in the large dining area, relaxing evenings spent in the expansive living room, and daylight hours spent in and around the heated pool. Clearly Ginger and Ken have perfected everything relating to this property and rental, from their commitment to upkeep to communications throughout the process.

We are forever grateful to Ginger and Ken for them entrusting us with their beautiful (& historic) property and for creating a venue where our family made memories lasting a lifetime. Our entire family so enjoyed our week together at Gentle Heritage that I foresee a family reunion at this location in the future.

On October 7, 2001, I got remarried at Gentle Heritage because it had the elegance and natural beauty that felt like the perfect match for the day that my fiancé said “I do” to me and my two young children – who were our Maid of Honor and Best Man. Seventeen years later, on October 7, 2018, my daughter chose Gentle Heritage again for her wedding day. She always remembered the fun she and everyone else had at our wedding, and wanted to recreate that for her day. It did not disappoint. We had 12 staying at the home, the weather cooperated, and the vendors were fantastic. If you use vendors that are familiar with the property, it makes everything go that much easier. The back kitchen was very handy to prep food and store excess refrigerated items. The owners renovated in 2010 and added another ½ bath to the property which was helpful the day of the wedding.

We spent leisure time at the expanded sandy beach in the front of the house and enjoyed corn hole games in the backyard. Ken and Ginger are prompt in responding to your questions before and during your stay. They have another home as you approach Gentle Heritage and were staying there during our visit. I highly recommend this property if you want to create a memory that will truly impact you for a lifetime.

We had the honor of hosting my daughter's wedding at the Winslow Estate's Gentle Heritage, and what a backdrop it provided! The bridesmaids and family stayed in the home for the week, while the groomsmen stayed at the property's Bay House. What a perfect situation! There was room for all, and it was so great to all be together as we approached the wedding.
We held the wedding in a tent overlooking the magnificent view. Our guests were just awestruck.

Everything went off without a hitch! Ken and Ginger were right there when we blew a fuse (ten bridesmaids, lol), helped with parking, and Ken even drove the bride, groom, and photographer down to a beautiful setting in his golf cart! They were helpful, yet utterly unobtrusive...you truly feel that this is your gorgeous home for the week.

Neither I nor our guests can say enough about this magical property!

Our dream for our wedding was to find a beautiful, charming beach house that could sleep our entire family and wedding party comfortably for the wedding weekend and also be suitable to have the wedding and ceremony there. I thought that was wishful thinking! When we found the Winslow Estate, it was a dream come true. The location is perfect, the views are breathtaking, and the estate and house layout are perfect for a large family. This family-run and -owned charming home has history, beauty and all of the amenities we needed to have the perfect weekend. I honestly cannot explain how amazing it was and how amazing Ken and Ginger were to work with as well. They provided every local recommendation we needed as well. From caterers and tents to supplies, restaurants and places for guests to stay for the wedding. All of which were fantastic recommendations. The town is beautiful and the house is located in the perfect private spot. It could not have been any better. By far a weekend that none of us wanted to end and one we will all cherish forever. This is highly recommended and if I could do it all again, I certainly would. Simply perfect.

This is a very special place not only to have a beautiful wedding, but to experience a loving week around your wedding with the people you love most. We found the house perfect for our taste and magical: it is beautiful, grand and special, but it still has a bit of a salty Cape Cod feel to it and it’s not overly opulent or stuffy. We and our guests felt comfortable and found it easy to make it home for a week. Our two families, one from Montana, the other from Cape Cod, piled 16 of us into the house beginning the Wednesday before our wedding and departing the Wednesday after the event. This gave us some special time to spend together before and after our day, and to properly prep and break down without the feeling of chaos that comes with having too little time.

Our nephews spent most of the week on the beach below the property’s bluff, our brothers shuttled us and friends on boats in and around Pleasant Bay, our parents sunned and drank wine on the patio, and all of us cooked meals together throughout the week. At some point we lost count of the champagne toasts. There is plenty of room for both groom, bride, family and friends to get ready here - you really create your own personal castle around your day. We also rented The Bay House next door, which we found to be the perfect accommodation for our wedding party (though accommodating other family or guests there would work great, too).

The pictures are accurate but the view is really better than one can capture. We were lucky to get a sunny day, but this property would be beautiful in any shoulder season weather.

Couples considering the property should be ready to coordinate the moving pieces of their wedding, or hire a planner to do so. The choices for tent rentals, caterers, and beyond are endless and we found that the charm of renting here is that you can really put your fingerprints on your day, but it does mean keeping an eye on many moving pieces (we really liked this part, but it’s not for everyone). We did all the details ourselves but hired someone to take over a few days before so that we could really enjoy. The nice thing about having your wedding here though, is that there is more than one way you can have your day and that is great for different tastes and budgets.

Ginger and Ken are wonderful hosts, and if we could impart any advice to those planning to have a wedding here, it would be to make sure you understand the rules and guidelines that they give you; they are all for good reasons and all important, but for a stress-free week, knowing all of these ahead of time is very helpful – and they are clear about almost everything ahead of time. Ginger answered our questions thoroughly and quickly during the months we planned our day. This is a unique and very special place for an event, and we are grateful to have had our wedding here and will remember it forever.

Our family of 27 had a wonderful week long vacation at the Winslow estate and bay house. The views were incredible from the back yard and veranda of Pleasant Bay. Our nightly happy hours and cookouts were the highlight of the vacation. The kids ran around in the yard playing games while the adults enjoyed music and cocktails. The house was clean and spacious with interesting architecture and details. The house was very spread out which accommodated the different parts of our family. We would love to come back in the future.

We rented Gentle Heritage and its accompanying guest house for a once-in-a-generation reunion with a clan of 28 and had an exceptional time. The property exceeded expectations in all regards. Spacious, beautiful, very comfortable, in great shape, and with unparalleled views and setting. Owners were incredibly gracious and easy to work with. This has our highest possible recommendation!

Our family celebrated our parents' 60th anniversary at this beautiful and unique home. With plenty of places to relax and take in the views thoughout the day and in the evenings, the setting was just perfect and for everyone it was a memorable week. Great thanks to our hosts/owners the Winslows, who were very welcoming, helpful and eager to offer ideas for dining and recreation. We loved our stay in this special home and hope to return!

To call the Winslow Estate spectacular doesn't even do it justice. I can only describe it as a little piece of heaven on Cape Cod. Everything was as promised, and Ken and Ginger were terrific to deal with. I held my daughter's wedding reception on the property and can't begin to tell you how happy we are that we did. Booking from Wednesday to Wednesday gives you time to settle I and time to relax after the event.

I would describe the estate as "A little piece of heaven on Cape Cod".....

Seventeen family members ages 16 to 82 gathered for a reunion. We came from Paradise Valley AZ, Mission KS, Austin TX, Overland Park KS, Key West FL and Evergreen CO. Only one person had ever been to Cap Cod.

As the event planner, I worried if the property would accommodate us comfortably; it did. We sometimes went our separate ways during the day visiting many interesting nearby places. Afterwards we looked forward to our big meal together, at what we all called home. Family members took turns cooking meals. With two kitchens there was never a problem with storage or work space. My contribution was a lobster dinner. The owners suggested I get steamed and cracked lobsters from the Nauset Fish Market and then just warm them up on the outdoor grill. We prepared delicious side dishes. Thanks to my son-in law's foresight, he stopped at Costco, located near Logan Airport, before arriving. I had him choose some nice red and white wines for the dinner. They were reasonably priced.

Those who were 55 and younger enjoyed hiking and biking. All of us enjoyed going to Provincetown whale watching. We saw 5 whales at one time. The JFK Museum was interesting. It’s small and easy to get through. Wherever we went, we found nice places for lunch.

It was memorable being in such a historic area on the 4th of July. That evening, from the patio, we watched the fireworks across the bay. I’d been told by the owner we would have arena seats. Their private beech offered much joy when everywhere else was crowded.

The owners were very helpful with answering my many questions. I was totally comfortable with the way they made sure our needs were met.

This was the second year that our group of nine adult women--all artists and/or writers--gathered for a long spring weekend at this gorgeous waterfront property. We knew from our first visit that the property is, if anything, even better than described: secluded yet not too remote, spotless, well-maintained, and spacious, with plenty of room to spread out. We each had our own charming bedroom for reading, writing, and napping; we also made full use of the shared spaces, such as the TWO fully stocked kitchens, the porches, the sunroom, and the living rooms, where we worked on projects, played games, or just hung out together. The owners are friendly, professional, and, above all, responsive. We expect to make this getaway an annual tradition at this venue, and some of us have already recommended it to friends and relatives. It's a real treasure.

Gentle Heritage is an absolutely spectacular property! The views from the bluff over-looking Pleasant Bay are gorgeous. Everything was very clean and well maintained. We were there for a family wedding (held elsewhere), so it was a perfect place for so many of us to gather for the weekend. Luckily, the weather was perfect and several people even enjoyed a dip in the water. The listing description was accurate and the owners were very helpful and accommodating. I highly recommend this property!

Although my fiancé and I are not from Cape Cod, we knew as soon as we got engaged that the Cape was the perfect destination for our wedding. Despite residing in Chicago, we researched from afar and narrowed our selection to 10 different venues/locations to visit the following month. Although we saw some amazing places, we knew in our heart the winner would be the Winslow Estate and upon arriving for our tour and driving up the entrance way, our decision was instantly made even before we got out of the car. Our criteria was simple: we wanted our ceremony and reception at the same location, preferably outside, where our wedding party was also able to stay through the weekend, and the Winslow Estate accommodated all the above.

To say the estate is beautiful is a complete understatement. The house itself, the yard, the views of Pleasant Bay are all breathtaking. Although I’ll admit the price was a bit of a surprise at first, we can say now it was 100% worth it. Once we decided that the Winslow Estate was right for us, the owners (Ken and Ginger) were incredibly helpful, responsive and supportive throughout the entire planning process; always available to answer questions via phone or e-mail or provide recommendations as needed. Given that we were planning a wedding from Chicago, this level of support was certainly needed! We were able to have ourselves and our entire wedding party sleep and stay at the estate leading up to the wedding. We had a smaller guest count (around 85) that all fit comfortably during both the ceremony on one side of the yard and then under a covered tent during the reception on the other side.

I’d recommend the Winslow Estate to anyone without hesitation whether for weddings, family reunions, etc. Our memories from our wedding day are priceless, largely due to the location we held it at.

Thank you, Ken and Ginger, for an amazing experience!
Best,
Laura & Greg Ott

The Gentle House was amazing for my wedding week. My husband and I were able to move in Wednesday and start the preparation for our wedding day that was on Saturday. My whole family came on Thursday and enjoyed the luxuries of the house and the beautiful scenery. The house was the perfect size for the 18 of us because we were not on top of each other and there was plenty of space to relax or enjoy the outdoors. The house had EVERYTHING you need for the week like linens, kitchen needs, laundry, games, beach toys, and cable / Internet. Everybody who attended the wedding could not believe the unbelievable view over the water and the amenities the house provided (clean bathrooms and patio to converse on). Ken and Ginger were a pleasure to work with and were very accommodating with anything needed. The week was amazing and well worth the cost of renting for the week.

Mike and Kate

f you are looking for "The Perfect Wedding Site"...look no further......in a special little corner of the world called Cape Cod is a another special place overlooking Pleasant Bay in Orleans MA. We had our daughter's wedding here at Gentle Heritage on a perfect autumn day in October 2008 and guests are STILL raving about it, months later, as the most beautiful wedding they have ever attended! They all loved roaming the house and the grounds. The bride & groom married here as well - couldn't ask for a more picturesque background than the sea for guests to enjoy during the ceremony!!! The estate housed the wedding party that all came from "off-Cape". That helped make the special day even more special with loved ones all around and close by before, the day of & after the wedding! More guests rented the Winslow's Bay House next door so it made it all the merrier! The accommodations of Gentle Heritage were wonderful - plenty of room for all with so many bedrooms and bathrooms - porch, dining room, living rooms and billiard room were ALL used and enjoyed!! The site itself sits with gentle pride overlooking a panoramic view of one of the quiet inlets of the Atlantic Ocean - Pleasant Bay. Guests at the wedding thought they were in Bermuda! The owners, Ginger & Ken could not have been any more gracious and accommodating! I have been amazed that so many that live here on the Cape are not familiar with this estate as it still seems to be a bit of a "secret place"....all the better for planning a special wedding day!!! You will certainly awe and dazzle your guests with it all I promise! No hotel or wedding site can surpass all that can be offered here...as there are NO other weddings happening here the day of yours! Or the day before or after!!! The week flies by, but you are left with heartwarming memories of a glorious seven days! I live in the town next to Orleans and love that I can still drive by Pleasant Bay and look across it and up to that hill and smile remembering the wonderful wedding we had there!!! I bet it's a perfect place for a family reunion as well! My daughter Jenn's hug and words said it all... "Thank you for the wedding of my dreams and the most perfect wedding ever!" Thank you Ginger and Ken for a wonderful week and all the memories we will cherish forever! Donna M.

We looked everywhere for a place on the Cape where we could have the kind of wedding we wanted - a beautiful setting, a place where friends and family could hang-out, the ability to have the kind of wedding we wanted (and not one planned by a resort/hotel/etc.). It was really difficult to find such a place since most private homes can't handle large groups of people. We feel incredibly lucky to have found the Winslow Estate and we had exactly the wedding we wanted here. We rented the space for the week and had our bridal party join us to hang out. We had a very small, low-key rehearsal on Friday night. And on Saturday we had a clam bake and played whiffle ball. I imagine this spot works just as well if you want a formal event, but for us it was the perfect place to have a laid-back, casual party at a gorgeous, comfortable location. I'm pretty sure there is no other place like it on the Cape.

Words cannot describe how wonderful this property is. We enjoyed an absolutely perfect week here with our family of 14 celebrating our parents' 50th wedding anniversary. We ranged in ages from 3 to 80 and absolutely everyone loved this house. The views of the water, from just about everywhere in the house or on the property, are breathtaking. The rooms are all spacious, bright, charminly decorated and extremely well mantained. There are plenty of places for people or groups (large or small) to escape to or gather in. The grounds, with the large open lawn and the private beachfront where the children played for hours on end, are simply gorgeous. Ken and Ginger are the perfect hosts---attentive, warm, welcoming and extremely helpful. They genuinely care about the house and anyone inhabiting it. It is hard to imagine a better property on Cape Cod. We fell in love with this house and desperately hope to return some day soon.