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Orleans Vacation Rental home in Cape Cod MA, short path leads down the bluff to private beach | ID 19054
9 BR
5 ½ baths
Sleeps 19
Beds: 1 king, 3 queens, 11 twins
Beach: short path leads down the bluff to private beach
Guest Reviews: 19 reviews
Daily
Weekly
Monthly
Off-season 2020/21
$2,500
Summer 2021
 
Off-season 2021/22
$2,400
Off-season 2020/21
$10,000 - $20,000
Summer 2021
$20,000 - $23,000
Off-season 2021/22
$14,000 - $17,000
Off-season 2020/21
 
Summer 2021
 
Off-season 2021/22
 
State and local taxes of 14.45% will apply
Contact: Ginger Winslow
Click to see contact phone numbers
Phone: (617) 413-1856
Time Active:
10+ years
3
Description

Description

We have it all - uniquely private location, private waterfront and sandy beach and now with a new heated 16.5' by 39' pool for the summer of 2020.Our waterfront estate on the Chatham line in South Orleans features 300 feet on beautiful Pleasant Bay, where it has been a landmark to the area for 100 years. We were chosen by Cape Cod Life magazine as one of the top places to rent on the Cape! The house sits on three acres on a peninsula overlooking the Bay, Quanset Pond, Chatham, Nauset Beach, and the Atlantic. The extensive lawn, with underground sprinklers, offers plenty of room for fun and sun between the 17 room house and the bluff and beach. New for 2020 is a pool, so between the beach and the pool, there's no need to leave the estate! A pathway leads down the bluff to the beach. The water is warm and calm. There is a deep sandy beach at low tide. This gets covered by the high tide, but there is a deck to sit and enjoy the sun and watch those swimming in the water, the kayakers, the paddleboarders, or just enjoy the view.

The estate is at the end of a private road - far away from any traffic and noise.The house offers plenty of room for everyone to gather together or to find some private space. The 17 rooms include 9 bedrooms, 5 and 1/2 baths, and 3 fireplaces. One bedroom has a king sized bed.Three bedrooms feature queen sized beds. The other 5 bedrooms have sets of twin beds and one has 3 twin beds. The bedrooms provide sleeping for 19 people. 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 twins beds, queens and one king. The second floor as well as two wings of the house are air conditioned. All bedrooms plus the family room and dining room have A/C.

The waterfront side of the house with a southern exposure features a large sunroom with sets of sliding glass doors, several porches, and a large terrace. The game room is a popular gathering place with a pool table and dart board. There are 2 living rooms each with a TV, VCR, DVD, and wireless internet access. The main kitchen was remodeled in 2001 with Corian countertops, a Sub-Zero refrigerator, microwave, dishwasher, disposal, ice cube maker, etc. The former servants wing has an additional modern kitchen that is equally fully equipped. There is a separate laundry room with washer and dryer. Everyone enjoys the fully enclosed outdoor shower. Beach, bed and bath linens included. No cleaning fee or taxes or hidden fees.

The estate is available for families, for groups, and for special gatherings by the week from June through September and by the week and week-end in the off season. The house is closed for the season after Thanksgiving and reopens in April.
There is a mooring available to bring your boat.
See a floor plan on our web site winslowestates.com
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See their private website.

Location

Location - Orleans

Nearest beach: short path leads down the bluff to private beach

41.7362550 -69.979260 0
Photos

Photos

Pricing & Availability

Pricing & Availability

1

Calendar Last Updated: November 04, 2020

Additional availability info: This is a Saturday to Saturday vacation rental.

Payment Methods: Personal checks

Additional pricing info: cleaning included. Linens included for weekly guests. Multiple week discount. State and local taxes of 14.45% will apply

Minimum Stay Requirements:
  • Off-season 2020/21
    2 nights
  • Summer 2021
    7 nights
  • Off-season 2021/22
    2 nights
Available
Unavailable
Unknown
  • Price JANUARY 2021
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  • Price MARCH 2021
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  • Price APRIL 2021
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  • Price MAY 2021
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  • Price JUNE 2021
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  • Price JULY 2021
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  • Price AUGUST 2021
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  • Price SEPTEMBER 2021
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  • Price OCTOBER 2021
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  • Price NOVEMBER 2021
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  • Price DECEMBER 2021
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  • Price JANUARY 2022
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  • Price FEBRUARY 2022
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  • Price MARCH 2022
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  • Price APRIL 2022
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  • Price MAY 2022
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  • Price JUNE 2022
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Amenities

Amenities

Proximity to water and beach
  • on a salt water beach
Interior
  • Central A/C
  • Washer & Dryer
  • Dishwasher
  • Microwave
  • Coffeemaker
  • Linens Included
  • Cable TV
  • DVD or VCR
  • Fireplace
  • Wireless or wired internet
  • No Smoking
Exterior
  • Screened Porch
  • Deck/Porch/Patio
  • Pool
  • BBQ-Grill
  • Outdoor Shower
Other
  • No Pets
Handicap Accessibility
  • 17 of the 19 rooms are on the first floor. The house is handicapped friendly.
Green Amenities
  • Eco-friendly cleaning supplies
  • Reusable grocery totes
  • ENERGY STAR appliances
Reviews

Guest Reviews

19 reviews
Have you stayed here? Write a review
Amazing -- Five stars!

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!

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Date of Stay: September 2020
Date Submitted: October 2020
Owner Response:

Thank you so much. We are so glad to know Gentle Heritage added many wonderful memories to your special day.

Winchester, MA
Member since Aug 2011
40th Birthday Celebration

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! show more show less

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Date of Stay: September 2020
Date Submitted: September 2020
Owner Response:

Thank you so much for your lovely review, Elizabeth. You were great guests.

Houston, TX
Member since Sep 2020
Wedding of a Lifetime

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.
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Date of Stay: September 2020
Date Submitted: September 2020
Owner Response:

What a lovely review, Patty!! Thank you for all you said and did. The wedding was wonderful and it always was a pleasure working with your family.

Attleboro, MA
Member since Sep 2020
Our 2nd wedding at this beautiful property!!

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.
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Date of Stay: October 2018
Date Submitted: October 2018
Harvard, MA
Member since Oct 2018
Beautiful memories for my daughter's wedding!

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!
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Date of Stay: September 2017
Date Submitted: October 2017
Sherborn, MA
Member since Oct 2017
Perfect, just perfect.

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. show more show less

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Date of Stay: September 2017
Date Submitted: September 2017
Plymouth, MA
Member since Aug 2010
A special, magical place for a wedding week

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.
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Date of Stay: September 2017
Date Submitted: November 2017
Member since Jan 2017
Great family reunion

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. show more show less

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Date of Stay: July 2017
Date Submitted: August 2017
Owner Response:

And, you and your family were most welcome guests. Thank you so much for taking the time to let others know about your vacation with us on Pleasant Bay. We hope you will return.

Columbia, MO
Member since Aug 2017
Outstanding Reunion Site!

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!

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Date of Stay: July 2017
Date Submitted: July 2017
Aurora, CO
Member since Jul 2017
A wonderful week with family!

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!

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Date of Stay: June 2017
Date Submitted: July 2017
Member since Jul 2017

About Ginger Winslow

Member since:
5/17/2010
Reviews:
19 reviews
This property has been in the family for over 100 years We are both (almost) cape codders having spent all our summers here, met and married here and have managed the property (now with our children and grandchildren) for over 40 years.

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