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

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.