Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.
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: 23 reviews 23 reviews
Daily
Weekly
Monthly
Summer 2022
 
Off-season 2022/23
$3,000
Summer 2023
 
Summer 2022
$20,000 - $23,000
Off-season 2022/23
$14,000 - $21,000
Summer 2023
$19,000 - $28,000
Summer 2022
 
Off-season 2022/23
 
Summer 2023
 
Listed by Ginger Winslow
Active
12+ years
Property ID 19054
3
Description

Description

We have it all - uniquely private waterfront location with 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. It is a landmark to the area. owned by the same family for over 100 years, and lovingly cared for and maintained to match the grandeur of times past with modern amenities. It is an ideal environment for multi generational family members to vacation together - or old friends - with lots of room to spread out, enjoy each others company, yet find privacy and peace. 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. 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 and 5 and 1/2 baths.. 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. There are no sofa beds, futons, trundle beds, bunk beds or cots. Everyone has a personal and private space. 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. The main kitchen has 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.. Everyone enjoys the fully enclosed outdoor shower. Beach, bed and bath linens included.for weekly rentals.

The estate is available for families and friends by the week from early June through late September. Please do not ask us about one- or two-day rentals. We will consider three-day rentals in May or October. The house is closed for the season after Thanksgiving and reopens in May.

See a floor plan on our web site winslowestates.com
read more show less

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

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:
  • Summer 2022
    7 nights
  • Off-season 2022/23
    3 nights
  • Summer 2023
    7 nights
  • Off-season 2023/24
    3 nights
Available
Unavailable
Unknown

Calendar Last Updated: August 03, 2022

next
  • Price AUGUST 2022
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $23,000      1 2 3 4 5
     $23,000  6 7 8 9 10 11 12
     $23,000  13 14 15 16 17 18 19
     $22,000  20 21 22 23 24 25 26
     $20,000  27 28 29 30 31    
  • Price SEPTEMBER 2022
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $20,000            1 2
     $20,000  3 4 5 6 7 8 9
     $20,000  10 11 12 13 14 15 16
     $20,000  17 18 19 20 21 22 23
     $20,000  24 25 26 27 28 29 30
  • Price OCTOBER 2022
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $17,000  1 2 3 4 5 6 7
     $17,000  8 9 10 11 12 13 14
     $17,000  15 16 17 18 19 20 21
     $17,000  22 23 24 25 26 27 28
     $17,000  29 30 31        
  • Price NOVEMBER 2022
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $17,000        1 2 3 4
     $14,000  5 6 7 8 9 10 11
     $14,000  12 13 14 15 16 17 18
     $14,000  19 20 21 22 23 24 25
     $14,000  26 27 28 29 30    
  • Price DECEMBER 2022
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $14,000            1 2
        3 4 5 6 7 8 9
        10 11 12 13 14 15 16
        17 18 19 20 21 22 23
        24 25 26 27 28 29 30
        31            
  • Price JANUARY 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
          1 2 3 4 5 6
        7 8 9 10 11 12 13
        14 15 16 17 18 19 20
        21 22 23 24 25 26 27
        28 29 30 31      
  • Price FEBRUARY 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
                1 2 3
        4 5 6 7 8 9 10
        11 12 13 14 15 16 17
        18 19 20 21 22 23 24
        25 26 27 28      
  • Price MARCH 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
                1 2 3
        4 5 6 7 8 9 10
        11 12 13 14 15 16 17
        18 19 20 21 22 23 24
        25 26 27 28 29 30 31
  • Price APRIL 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
        1 2 3 4 5 6 7
        8 9 10 11 12 13 14
        15 16 17 18 19 20 21
        22 23 24 25 26 27 28
        29 30          
  • Price MAY 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
            1 2 3 4 5
        6 7 8 9 10 11 12
     $15,000  13 14 15 16 17 18 19
     $15,000  20 21 22 23 24 25 26
     $15,000  27 28 29 30 31    
  • Price JUNE 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $15,000            1 2
     $17,000  3 4 5 6 7 8 9
     $17,000  10 11 12 13 14 15 16
     $21,000  17 18 19 20 21 22 23
     $22,000  24 25 26 27 28 29 30
  • Price JULY 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $25,000  1 2 3 4 5 6 7
     $25,000  8 9 10 11 12 13 14
     $25,000  15 16 17 18 19 20 21
     $28,000  22 23 24 25 26 27 28
     $28,000  29 30 31        
  • Price AUGUST 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $28,000        1 2 3 4
     $28,000  5 6 7 8 9 10 11
     $23,000  12 13 14 15 16 17 18
     $23,000  19 20 21 22 23 24 25
     $23,000  26 27 28 29 30 31  
  • Price SEPTEMBER 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $23,000              1
     $19,000  2 3 4 5 6 7 8
     $19,000  9 10 11 12 13 14 15
     $19,000  16 17 18 19 20 21 22
     $19,000  23 24 25 26 27 28 29
     $19,000  30            
  • Price OCTOBER 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $19,000    1 2 3 4 5 6
     $18,000  7 8 9 10 11 12 13
     $18,000  14 15 16 17 18 19 20
     $17,000  21 22 23 24 25 26 27
     $17,000  28 29 30 31      
  • Price NOVEMBER 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $17,000          1 2 3
     $16,000  4 5 6 7 8 9 10
     $16,000  11 12 13 14 15 16 17
     $16,000  18 19 20 21 22 23 24
     $16,000  25 26 27 28 29 30  
  • Price DECEMBER 2023
      Sa
    Su
    M
    Tu
    W
    Th
    F
     $16,000              1
        2 3 4 5 6 7 8
        9 10 11 12 13 14 15
        16 17 18 19 20 21 22
        23 24 25 26 27 28 29
        30 31          
  • Price JANUARY 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
            1 2 3 4 5
        6 7 8 9 10 11 12
        13 14 15 16 17 18 19
        20 21 22 23 24 25 26
        27 28 29 30 31    
  • Price FEBRUARY 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
                  1 2
        3 4 5 6 7 8 9
        10 11 12 13 14 15 16
        17 18 19 20 21 22 23
        24 25 26 27 28 29  
  • Price MARCH 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
                    1
        2 3 4 5 6 7 8
        9 10 11 12 13 14 15
        16 17 18 19 20 21 22
        23 24 25 26 27 28 29
        30 31          
  • Price APRIL 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
            1 2 3 4 5
        6 7 8 9 10 11 12
        13 14 15 16 17 18 19
        20 21 22 23 24 25 26
        27 28 29 30      
  • Price MAY 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
                1 2 3
        4 5 6 7 8 9 10
        11 12 13 14 15 16 17
        18 19 20 21 22 23 24
        25 26 27 28 29 30 31
  • Price JUNE 2024
      Sa
    Su
    M
    Tu
    W
    Th
    F
        1 2 3 4 5 6 7
        8 9 10 11 12 13 14
        15 16 17 18 19 20 21
        22 23 24 25 26 27 28
        29 30          
next
Amenities

Amenities

  • On a salt water beach On a salt water beach

  • Central air Central air

  • A/C unit(s) A/C unit(s)

  • Outdoor shower Outdoor shower

  • Washer&dryer Washer&dryer

  • Swimming pool Swimming pool

  • No Pets No Pets

  • Internet Internet

  • Linens provided Linens provided

  • Screened porch Screened porch

  • Deck, porch or patio Deck, porch or patio

  • BBQ-grill BBQ-grill



    Green Amenities

    3
    • ENERGY STAR appliances ENERGY STAR appliances

    • Eco-friendly cleaning supplies Eco-friendly cleaning supplies

    • Reusable grocery totes Reusable grocery totes

    Reviews

    Guest Reviews

    23 reviews
    Have you stayed here? Write a review
    Beautiful rental property & wedding venue

    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.

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: May 2022
    Date Submitted: July 2022
    Lindsay T.
    Dennis, MA
    Member since Jul 2022
    The Best Wedding Venue

    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.
    show more show less

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: October 2021
    Date Submitted: October 2021
    Owner Response:

    Thank you so much. It was a lovely wedding. You both were wonderful to work with throughout all the dates and changes. We are very happy all went beautifully. Five stars for your family!

    Caitlin F.
    Boston, MA
    Member since Oct 2021
    Gentle Heritage

    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.
    show more show less

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: June 2021
    Date Submitted: July 2021
    Sue V.
    Hingham, MA
    Member since Jul 2021
    A timeless Wedding venue and experience

    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
    show more show less

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: May 2021
    Date Submitted: July 2021
    Peter C.
    Boston, MA
    Member since Jul 2021
    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!

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    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.

    Peter B.
    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

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: September 2020
    Date Submitted: September 2020
    Owner Response:

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

    Elizabeth A.
    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.
    show more show less

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    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.

    Patty A.
    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.
    show more show less

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: October 2018
    Date Submitted: October 2018
    Janet S.
    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!
    show more show less

    Date of Stay: September 2017
    Date Submitted: October 2017
    CAROL H.
    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

    Accuracy of listing:
    Cleanliness of home:
    Experience with homeowner:
    Return to rental or recommend to friend:
    Date of Stay: September 2017
    Date Submitted: September 2017
    Cristen S.
    Plymouth, MA
    Member since Aug 2010
    About

    About Ginger Winslow

    Member since:
    5/17/2010
    Reviews:
    23 reviews
    Response Time:
    Within a day
    Response Rate:
    98%
    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.

    Contact
     
     
    Your Email
     
    First Name
     
    Last Name
    Describe Your Dates
    Phone (optional)
    # Guests
    Adults
    Children
    Done
    Describe yourself, what you're looking for, and ask questions!
    Message
    Not from the United States?
    Country
    Send As Guest
    Clear Form