Waterfront. Private beach. Pool. Estate has it all!!
House in Orleans, MA
19 guests · 9 bedrooms · 7 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Chosen by Cape Cod Life magazine as one of the Top Ten places to stay on Cape Cod. Our waterfront estate now has a gorgeous heated pool plus breathtaking views of over 180 ' plus of Pleasant Bay and 300' of your own PRIVATE waterfront. Plus you are directly on the water, not across the street or down the lane. This very special property is a landmark to the area and owned by the same family since it was built on the shores of Pleasant Bay 100 years ago. It had been lovingly cared for and maintained and matches the grandeur of times past with modern amenities. It is an ideal environment for multi generational family members to vacation together - or old or new friends with lots of room to spread out, enjoy each others company, yet find privacy and peace.
Down the end of an old cape cod road, then down the end of a private seashell driveway, there are no streets, traffic, or even pedestrians nearby. Pleasant Bay is reached by a pathway down the bluff in front of the house. Although the sandy beach disappears during a high tide, there is a deck to sit on until the beach reappears. The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore. The new heated pool and deck area are sun filled and full of fun for all ages. There is a gas barbecue grill, seating for your family group, lounge chairs - everything you need for fun. The pool is open and heated from mid June until Labor Day.
There are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor showe. All of the bedrooms plus the dining room and family room are air conditioned. The kitchen features a 48' refrigerator, Corian counters, plus the estate includes a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table, private deck on the beach and the pool and pool terrace. .The pool is 16.5' by 39'.
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The nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twin beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large bedroom that has three twin beds.
Beach, bed and bath linens are included for weekly rentals. Weekenders please plan to bring your own or use one of the local linen services. The cleaning fee is included for weekly rentals. Available by the week only from early June to late Sept. Please do not ask us about one or two night stays. The minimum is three nights and only occasionally in May or October. See a floor plan at our web site winslowestates.com.
Summer rentals are Friday to Friday so you can avoid all the headaches of the more typical Saturday with hours of backed up traffic. Great to include family and friends who otherwise could not enjoy a weekend with you.
Cancellation Policy - all payments returned upon ability to re-rent the same time period for the same amount.
Down the end of an old cape cod road, then down the end of a private seashell driveway, there are no streets, traffic, or even pedestrians nearby. Pleasant Bay is reached by a pathway down the bluff in front of the house. Although the sandy beach disappears during a high tide, there is a deck to sit on until the beach reappears. The Bay has a gradual sandy bottom, warm water great for swimming, floating on rafts, paddle boarding, sailing, kayaking, and walking along the shore. The new heated pool and deck area are sun filled and full of fun for all ages. There is a gas barbecue grill, seating for your family group, lounge chairs - everything you need for fun. The pool is open and heated from mid June until Labor Day.
There are 3 acres of open lawn, 17 rms, 9 bedrms, 5 1/2 baths plus an enclosed outdoor showe. All of the bedrooms plus the dining room and family room are air conditioned. The kitchen features a 48' refrigerator, Corian counters, plus the estate includes a 2nd fully equipped kitchen. There is lots of room for everyone to spread out with three living rooms, game room with pool table, private deck on the beach and the pool and pool terrace. .The pool is 16.5' by 39'.
.
The nine bedrooms are really nine bedrooms - not common rooms that become bedrooms at night with pull out sofas. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. All of the bedrooms have twin beds or queens. The master bedroom has a king bed. Each bedroom sleeps two guests except for one extra large bedroom that has three twin beds.
Beach, bed and bath linens are included for weekly rentals. Weekenders please plan to bring your own or use one of the local linen services. The cleaning fee is included for weekly rentals. Available by the week only from early June to late Sept. Please do not ask us about one or two night stays. The minimum is three nights and only occasionally in May or October. See a floor plan at our web site winslowestates.com.
Summer rentals are Friday to Friday so you can avoid all the headaches of the more typical Saturday with hours of backed up traffic. Great to include family and friends who otherwise could not enjoy a weekend with you.
Cancellation Policy - all payments returned upon ability to re-rent the same time period for the same amount.
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Wheelchair accessible
Garden
Family friendly
Map of Orleans, MA
$$$$
Ratings and reviews
Summary of reviews
The Winslow estate is perfect for family gatherings, weddings, and special events. The property offers stunning views, spacious accommodations, and attentive hosts. Highly recommended for unforgettable experiences.
10.0 / 10.0
Amazing hosts on an amazing property!!
Beautiful views and attention to small details - like the clean linen was on the bed for us!! And the welcoming basket!!
Thanks so much for the memories!!
10.0 / 10.0
The Winslow estate was the perfect spot for our family vacation. Three generations enjoyed every aspect of the property. Ken and Ginger were a pleasure to work with.
10.0 / 10.0
This property is just as stunning and beautiful as the pictures show. We were at maximum capacity with 19 people (4 families) and we never once felt crowded or that we didn’t have enough room. Amazing. Loved the historic nature of the house that’s over 100 years old but that also included modern updates where it mattered the most (bathrooms, beautiful new pool). With Covid we barely left the property but you didn’t have to!!! Such a fun and relaxing week. We felt like we were the Kennedys on the compound for a week! Ken and Ginger were very responsive to any questions or issues. Highly recommend.👍
10.0 / 10.0
We were looking for a place that could accommodate our extended family and friend’s reunion on Cape Cod. Ken and Ginger’s historic home overlooking Pleasant Bay was exactly what we were looking for. The house absorbed the comings and goings of 25 guests over the two week stay. The location was breathtaking, the house met our needs and Ken and Ginger couldn’t have been more accommodating. Nothing is perfect. The house is a bit funky and looks more like a Bermuda cottage resort than Cape Cod, but it’s clean, well equipped, beautifully situated and everyone thoroughly enjoyed being there. If I could change anything it would be to add another bathroom or two. Nine bedrooms and 5 bathrooms require some flexibility, but we made it work. We recommend it highly to anyone planning an important family event.
10.0 / 10.0
Our Bookclub of 6 couples stayed at Ken and Ginger's home this past weekend. We found the homeowners to be a pleasure to work with and each one of us had a great time.
The home is well appointed with plenty of space and a fantastic water view with many areas to gather or find space if you need to. The kitchen and dining room easily held all of us. The pool table and dart board were a nice bonus!
10.0 / 10.0
We brought the entire extended family to celebrate our parents' 50th wedding anniversary and we could not have been happier with Gentle Heritage. The home is enormous, giving everyone the space they needed and also the common areas to all meet up for meals, chatting or just enjoying the incredible views of Pleasant Bay. The house is up to date, charming and we could not have asked for a better location. The Winslows were very attentive to our needs and made for very gracious hosts. We ranged in ages from 5 to 75 and the home worked for all of us. The private beach was so great for days we didn't want to leave the compound...and we found that we really didn't need to as we had everything we needed at the house. We were all very sad to leave, but plans to return are already in the works! Thanks again to the Winslows for sharing their amazing home with us. A trip to remember!
10.0 / 10.0
Must concur with the rave reviews of others. Gentle Heritage estate is unique and magnificent. Gorgeous grounds in a prime Cape Cod location. Ginger and Ken could not have been any kinder in all of their communications and accommodations. Highly recommend this estate and you can rest assured that it will be a pleasant experience with the Winslows.
10.0 / 10.0
A superb venue; a persistent rain the first day couldn't dampen the great fun experienced by 6 couples while staying for a get-away at this magnificent property. The charming accommodations, fine food, many nearby leisure pursuits and breath taking vistas of the wild beauty of Cape Cod were only exceeded by the warmth & genuine hospitality of the Winslows.
10.0 / 10.0
I rented the Winslow Estate for my daughter's wedding. Renting from Wednesday to Wednesday gave us all time to get settled in and time to relax after the fact. As I stated above to call the estate spectacular is truly an understatement. Everything was as promised. Ken & Ginger were great to deal with. I would strongly recommend this property to anyone. A little piece of heaven on Cape Cod!
10.0 / 10.0
If you're looking for that special place to hold your wedding, look no further. Unlike a resort venue with packaged plans, at the Winslow Estate you can make your wedding your own. The owners, Ken and Ginger, are eager to help you pull the pieces together with suggestions and lists of auxiliary vendors. Don't be deterred by the idea of an afternoon wedding. Nothing was more romantic than the tent coming alive for dinner and dancing after enjoying mid afternoon cocktails and fantastic views of Pleasant Bay in the bright sunshine. Not to mention the brilliant sunset enjoyed by all the guests! There was plenty of room for the entire wedding party and spouses to stay at the estate and they enjoyed their own post-wedding hang time together in a very relaxed, fun space. The Winslow Estate is the perfect wedding venue!
10.0 / 10.0
My husband and I have stayed there for my birthday. We had a fantastic time! The owners ken and ginger are awesome and were very accommodating to our needs. We had a great time. We are planning on coming back here again next summer.
5.0 / 10.0
From the moment we stepped on this property, with its magnificent, panoramic view of the bay, we knew it would be perfect for our daughter’s wedding. We had visited all the best venues on the Cape and this place was special. We rented Gentle Heritage for a week and arranged for the entire wedding party to stay with us. The owners were very pleasant, organized and helpful with logistics before the wedding. With plenty of rooms and lots to do on the property, we all had a fantastic time. Gentle Heritage has great facilities, spacious common rooms, many bedrooms and bathrooms, two kitchens, a billiards room, big backyard, and two pathways leading down to the beach. The bedrooms are well-appointed and comfortable. A family member brought his boat (there is public boat access nearby) and a few of us had a great time boating around Orleans and Chatham. The wedding was fabulous. So many of our guests commented that the property was the most beautiful they had ever been to for a wedding. With its breathtaking view of the bay and surrounding area, and perfect summer weather, it was truly a special day.
5.0 / 10.0
This house is incredible. My husband and I recently got married at the house. We had our closest friends and family stay with us for a week. All of our wedding guests were blown away with the views. The house has plenty of bedrooms and hangout space. It is also easy to access the water. We cannot wait to go back and spend anniversaries there.
5.0 / 10.0
Wow. Gentle Heritage has everything you need for a memorable stay on Pleasant Bay! This home delivers on everything in the summary, other renters’ reviews, and so much more. Gentle Heritage is very spacious and allows for multiple activities to happen at the same time or you can all hang out together in the living room or, even better, the beautiful outdoor space. The view is absolutely spectacular and I recommend enjoying it as often as possible during your stay.
I rented the property for a full week and it also hosted my 75 guest wedding. It could not have been more perfect. With so many rooms the Bride and Groom can each get ready at the house without the risk of seeing each other beforehand. The yard overlooking the bay makes for the best location for both ceremony and reception. Walking down to the deck by the beach makes for breathtaking photos. So much of the estate will become a part of your special day.
The owners are so helpful! Whether just staying with your family for the week or trying to plan a wedding, they are quick to respond to any message and accommodating your unique needs. They made our stay everything we wanted it to be, and more.
5.0 / 10.0
I take full credit for finding Gentle Heritage, Winslow Estate. Being an owner of a second property on Cape Cod, my daughter felt that her wedding should be on the Cape since we are on Cape as much as possible during the year. Besides the location and the property being so unique and gorgeous, especially when you have a day like we had weather-wise, the fact that the wedding party gets to stay there days before the wedding and after if they so choose is a bonus!! I truly believe that this allowed the wedding party to bond before the big day. It was also nice that we were the only wedding going on at the venue, unlike most places we looked at. We were constantly asked throughout the day, "how did you find this place" so we were thrilled with how everything turned out. So, from a wedding standpoint, it's a 10 in our opinion.
5.0 / 10.0
In our family's week long stay at Gentle Heritage we were sixteen ranging from 92 to 18 and unanimous in our enjoyment of the house, its location, views, comfort and amenities. We have stayed in large vacation homes in about ten different countries but this house tops them all.
Loet V. Sheffield, MA
5.0 / 10.0
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.
5.0 / 10.0
The Winslow Estate was the most magical venue to hold our daughter and son in law's wedding! The kind hosts were most accommodating with any of our needs! Our guests flew in from all over the world and everyone was so taken back by the beautiful setting! We will cherish our memories of this very special event in our lives!!!
Paul & Denise Graves
5.0 / 10.0
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!
5.0 / 10.0
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!
5.0 / 10.0
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
FAQs
How much does this house cost compared to others in Orleans?
The average price for a rental in Orleans is $403 per night. This rental is $1,955 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Waterfront. Private beach. Pool. Estate has it all!!. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Waterfront. Private beach. Pool. Estate has it all!!. Enjoy the water!
Is Waterfront. Private beach. Pool. Estate has it all!! pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Waterfront. Private beach. Pool. Estate has it all!!?
We found 13 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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