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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: 31 reviews 31 reviews
Daily
Weekly
Monthly
Off-season 2023/24
$3,000
Summer 2024
 
Off-season 2024/25
$3,500
Off-season 2023/24
$20,000
Summer 2024
$23,000 - $27,000
Off-season 2024/25
$17,000 - $23,000
Off-season 2023/24
 
Summer 2024
 
Off-season 2024/25
 
Listed by Ginger Winslow
Active
13+ 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 48'' 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. Our bookings are usualty Friday to Friday as our returnign guets much prefer to get in before the crazy Saturday/ Sunday traffic. This way you arrive and hae the wekend in front of you for family and friends.
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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
Minimum Stay Requirements:
  • Off-season 2023/24
    3 nights
  • Summer 2024
    7 nights
  • Off-season 2024/25
    3 nights
  • Summer 2025
    7 nights
Available
Unavailable
Unknown

Calendar Last Updated: January 22, 2024

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

Payment Methods: Personal checks

Other Fees:

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

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

    31 reviews
    Have you stayed here? Write a review
    Our Wedding

    We are so happy we got married at this Estate. My sister also got married here about 8 years ago so it's a very special place for my family as some of the best memories of our lives have been made here. The Estate itself is beautiful inside and out - it has such a unique look, stunning views of Pleasant Bay, and some of the best sunsets on Cape Cod. The property is extremely well-kept and the owners continue to invest in the property and make renovations/improvements to update the estate while still preserving its original character.

    But the Estate is so much more than it's beautiful aesthetic: it's a private, family-owned estate that provides the perfect venue for an intimate and customized wedding. Unlike several other venues, no wedding here is the same as the last. You truly have the autonomy to make it your own and make the look and feel represent you as a couple, making the day feel that much more special.

    The owners were extremely helpful throughout our wedding planning process. They have a great process in place for things like parking on the day of your wedding and they've built great relationships with key wedding vendors across Cape Cod, which helped our wedding go off without a hitch! And best of all, the owners are lovely. They made us feel so welcomed and comfortable on their property and we are forever grateful.

    This is a special venue owned by special people! Highly recommend getting married or doing an event here.
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    Date of Stay: September 2023
    Date Submitted: October 2023
    Owner Response:

    Thank you so much for this lovely review. We very much enjoyed working with you both and wish you the best in the years to come.

    Jaimie C.
    Charlestown, MA
    Member since Oct 2023
    A perfect mansion for a perfect backyard wedding

    This is an incredible property that can sleep your entire family & friends for a dream wedding. It overlooks a 270 degree bay and you get a dream sunset as an added bonus. I cannot possibly recommend this enough — every one of our guests said it was the most beautiful wedding they had ever been to.

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    Date of Stay: September 2023
    Date Submitted: September 2023
    Owner Response:

    Thank you for this lovely review! You were a pleasure to work with. And, yes that was a sunset to always remember. We are so pleased to have it happen for you both!

    James B.
    Orleans, MA
    Member since May 2022
    Amazing Wedding Week

    We could not have picked a better location to spend a week with our close family and friends and celebrate our wedding. The Estate is such a stunning venue and Ginger and Ken made planning our wedding very straightforward with recommendations and advice for what has worked well onsite. They also handled all guest parking on the day of our event and let us focus on celebrating.

    The bedrooms were beautiful and the bathrooms updated. Two kitchens allowed for easy meal prep and serving a crowd and we enjoyed some hot September days in the gorgeous pool overlooking Pleasant Bay. As someone who grew up on the Cape sailing and spending time on the water, it was such a treat to see this property from the other side. Truly a special place! show more show less

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    Date of Stay: September 2023
    Date Submitted: September 2023
    Owner Response:

    it was wonderful to have your nice family here. We look forward to seeing more of you around Orleans. Best wishes on you both in the years to come.

    Rachel L.
    Orleans, MA
    Member since Sep 2023
    Winslow Estate Gentle Heritage

    Our family stayed at this beautiful property for about 7 summers about 30 years ago. And so, I had high expectations when we decided to return with our grown children and grandchild. And the home was very much the same with some fabulous additions. First, the view of Pleasant Bay and the spacious grounds were still gorgeous. The house is sturdy, soundproof and can easily house many family members or friends. And the new additions such as a beautiful heated pool, ensuite bathrooms , outdoor shower, modern large grill, pool table, air conditioning made our stay even more enjoyable. There is also a covered outdoor area and a large enclosed porch for gathering areas in addition to the great room and second living area. There is a very large dining room table for family meals and another smaller dining table in another adjoining room. We had family meals nightly at the home which were easy with the well equipped kitchen and we enjoyed a private chef cooking dinner for us one evening. There is still a little beach area at the bottom of a little hill on the property - certainly good enough for sand play with a little one. The home is so special and obviously much loved by its owners, Ken and Ginger Winslow. And Ken and Ginger are so easy to deal with- They remembered us from so many years ago, they responded to email questions promptly and they returned my security deposit within days of our departure. We were so happy to be able to book for next summer - a true sign of a great vacation if you want to return before you have left.
    And you really don't ever need to leave the property except to go to the grocery store. Absolutely everything is onsite- plenty of dishes, 2 refrigerators, large dining tables, a small beach , a heated pool and beautiful, relaxing views. And most importantly, I have family and friends who want to make new memories with me to go along with my older ones at this gorgeous family home.
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    Date of Stay: September 2023
    Date Submitted: September 2023
    Owner Response:

    What a lovely review! Thank you so much. It was lovely to have you all back - after so many years. We look forward to seeing you again in 2024.

    Claire F.
    Providence, RI
    Member since Jan 2023
    Gentle Heritage - Late August/early September visit

    We held a multi-generational family reunion at Gentle Heritage - from 74 years old to 2 two year olds. It is a beautiful property with gorgeous grounds that are well maintained. It has a fabulous pool that everyone enjoyed. The house has plenty of space for a party of 13 - lots of nooks and crannies and great porches. The kitchen(s) were well equipped with plenty of nice dinnerware and also outdoor dinnerware and glasses. There were even plenty of beach chairs and beach and pool toys.

    We had a photographer down from Boston and took lots of family photos - she was in awe of the grounds and all the possible photo places.

    Gentle Heritage as lots of Cape Cod charm and we would highly recommend it for a family event.
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    Date of Stay: August 2023
    Date Submitted: September 2023
    Pamela R.
    Naples, FL
    Member since Sep 2022
    Gentle Heritage Estate

    This vacation for all members of my family from ages 76-8 far exceeded my expectations. The floor plan, the pool, pool table, spacious living room & small fun living room when the youngsters went to bed was absolutely perfect. It will be an memory etched in my heart forever. I would recommend this vacation spot for anyone that loves family or work retreats.

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    Date of Stay: June 2023
    Date Submitted: July 2023
    Owner Response:

    Thank you for sharing those fun pictures of your family. What a great bunch!. So glad you had a wonderful time.

    Christine M.
    Sterling, MA
    Member since May 2022
    Family gathering Celebrating a life well lived!

    My family, mother, children, grandchildren and great grandchildren gathered to celebrate the life of my father. 50 years ago we would walk below this bluff to go clamming. We would sail and waterski in the bay with this classic home looking down over us. It was my fathers happy place. Both indoors and out, this is the quintessential Cape Cod experience. The spaces inside and around the property provide for large gatherings, intimate conversations and private reflection.
    You can sense the history of gatherings taking place over the past decades. If you can't enjoy this home, property and surrounding views then you simply can't enjoy all the Cape has to offer. If it's the people/family gathering to celebrate living a good life, past, present and future, this is the perfect place!
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    Date of Stay: October 2022
    Date Submitted: December 2022
    Owner Response:

    This is lovely to read Bud. We are so pleased you all had a special time.

    Bud S.
    Hingham, MA
    Member since Dec 2022
    Perfection!

    What a gorgeous setting for a wedding! The grounds of this estate, with the views of Pleasant Bay, the beautifully maintained lawn along with the comfort of a spacious and comfortable large home made this the perfect place to hold our daughter's wedding. Our guests could not stop commenting on the beauty of the venue which made the whole weekend magical. Just as important, Ginger and Ken the owners, could not have been nicer or more accommodating. They were responsive, clear and easy to communicate with every step of the way. Our daughter and new husband stayed on to enjoy a short mini-moon and loved their stay, enjoying the well maintained pool and the waterfront.
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    Date of Stay: September 2022
    Date Submitted: October 2022
    Susan F.
    Brookline, MA
    Member since Oct 2022
    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.

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    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.
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    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
    About

    About Ginger Winslow

    Member since:
    5/17/2010
    Reviews:
    31 reviews
    Response Time:
    Within a day
    Response Rate:
    100%
    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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