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Waterfront Estate with Private Beach on Chatham Line
Orleans Vacation Rental - ID 19054

9 BR
5 ½ baths
Sleeps 19
Beds: 9 BRs: 1 king, 3 queens, 11 twins
Beach: short path leads down the bluff to private beach
Guest Reviews: 15 reviews
Daily
Weekly
Monthly
Off-season 2017/18
$1,500 - $2,800
Summer 2018
 
Off-season 2018/19
 
Off-season 2017/18
$10,000 - $18,000
Summer 2018
$18,000 - $19,000
Off-season 2018/19
$16,000 - $18,000
Off-season 2017/18
 
Summer 2018
 
Off-season 2018/19
 
Contact Ginger Winslow - ID 19054
Time active: 7 years, 6 months
Phone(s): (781) 749-1856 Phone(s): (781) 749-1856

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Description

Description

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. It was 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. 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.

Photos

Photos

Pricing & Availability

Pricing & Availability

0

Calendar Last Updated: December 15, 2017

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

Minimum Stay Requirements:
  • Off-season 2017/18
    2 nights
  • Summer 2018
    7 nights
  • Off-season 2018/19
    2 nights
Available
Unavailable
Unknown
 
  • Price DECEMBER 2017
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     $10,000              1
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        30 31          
  • Price JANUARY 2018
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  • Price FEBRUARY 2018
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  • Price MARCH 2018
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  • Price APRIL 2018
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  • Price MAY 2018
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     $16,000  5 6 7 8 9 10 11
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  • Price JUNE 2018
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     $16,000              1
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     $18,000  16 17 18 19 20 21 22
     $18,500  23 24 25 26 27 28 29
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  • Price JULY 2018
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     $19,000    1 2 3 4 5 6
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  • Price AUGUST 2018
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     $19,000          1 2 3
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  • Price SEPTEMBER 2018
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     $18,000  1 2 3 4 5 6 7
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     $16,000  29 30          
  • Price OCTOBER 2018
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     $16,000      1 2 3 4 5
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     $16,000  27 28 29 30 31    
  • Price NOVEMBER 2018
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     $16,000            1 2
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  • Price DECEMBER 2018
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  • Price JANUARY 2019
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  • Price FEBRUARY 2019
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  • Price MARCH 2019
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  • Price APRIL 2019
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  • Price MAY 2019
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  • Price JUNE 2019
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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
  • BBQ-Grill
  • Outdoor Shower
Other
  • No Pets
Handicap Accessibility
  • 17 of the 19 rooms are on the first floor. The house is handicapped friendly.
Location

Location - Orleans

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

41.7362550 -69.979260 0
Reviews

Guest Reviews

15 reviews
Have you stayed here? Write a review
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
The Winslow Estate in Orleans, MA

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"..... show more show less

Date of Stay: October 2016
Date Submitted: October 2016
Westborough, MA
Member since Oct 2016
Cape Cod Memories

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.
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Date of Stay: July 2016
Date Submitted: August 2016
Paradise Valley, AZ
Member since Aug 2016
The perfect spot for a group retreat/getaway!

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. show more show less

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Date of Stay: May 2015
Date Submitted: May 2015
Braintree, MA
Member since May 2015
Spectacular Property

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! show more show less

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Date of Stay: October 2014
Date Submitted: October 2014
Marshfield, MA
Member since Oct 2014

About Ginger Winslow

Member since:
5/17/2010
Reviews:
15 reviews
Calendar Last Updated:
12/15/2017