South Orleans Rentals USA Massachusetts Orleans South Orleans

Waterfront. Private beach. Pool. Estate has it all! | House in Orleans

10.0 (35 Reviews) |   9 Bedrooms  5 Bathrooms  19 Guests  Stay&Play
South Orleans House | Waterfront. Private beach. Pool. Estate has it all!

9 Bedroom House in South Orleans, Orleans

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. The 2 lofts have privacy walls and doors are accessed by staircases - on the west end thru the triple bedrm and on the east end thru the primary bedrm.
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.

Waterfront Private beach Pool Estate has it all! is located in South Orleans. Waterfront Private beach Pool Estate has it all! provides accommodation, featuring Wellness Facilities, Child Friendly, Private Pool, among other amenities. This House features Wellness Facilities, Child Friendly, Private Pool, to make your stay a comfortable one.

Waterfront Private beach Pool Estate has it all! has 9 Bedrooms , 5 Bathrooms, and max occupancy of 19 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the South Orleans has interesting places to visit. If you want to learn more about the House in South Orleans, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pool
  • TV
  • View
  • Private Pool
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Accessibility
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 3:00 pm contactless check-in available minimum check-in age: 30
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Note from host: ask owner pets not allowed
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: ask owner onsite parties or group events are strictly prohibited property registration number c0059852240 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Orleans, 02662, USA

What Our Guests say 500 + Reviews

Aug 17, 2024 05:29:09 AM
Summary: 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!!
Korey R. Korey R.
Jul 11, 2022 08:07:15 PM
Summary: 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.
Angelique C. Angelique C.
Aug 26, 2020 06:13:01 AM
Summary: 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.👍
Laura K. Laura K.
Aug 27, 2019 09:47:19 AM
Summary: 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.
Jack C. Jack C.
Nov 7, 2018 10:16:23 PM
Summary: 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!
Ayaz M. Ayaz M.
Sep 9, 2018 10:47:14 PM
Summary: 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!
Doug M. Doug M.
Nov 28, 2017 11:43:01 AM
Summary: 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.
Christopher C. Christopher C.
May 9, 2017 08:52:48 AM
Summary: 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.
Matthew C. Matthew C.
Oct 20, 2016 11:23:06 PM
Summary: 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!
Robert K. Robert K.
Oct 19, 2016 08:49:04 AM
Summary: 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!
Susan F. Susan F.

FAQ's

Is this South Orleans house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the South Orleans house have a swimming pool?

Yes, this South Orleans house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in South Orleans house?

Best-rates for the South Orleans house starts from $1,899 per night with includes Air Conditioner, Parking, TV, Balcony/Terrace, Sports/Activities, Fireplace/Heating, Pool, View, Security/Safety, Bedding/Linens, Barbecue/Outdoor Cooking, Kitchen, Laundry, Oceanfront, Accessibility, Wellness Facilities, Child Friendly, Private Pool, Ocean View, Entertainment, Internet StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is South Orleans house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the South Orleans house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the South Orleans house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the South Orleans house?

Based on the information reported by the owner or manager, the South Orleans house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for South Orleans house?

Based on the information reported by the owner or manager, details for the cancellation policy for the South Orleans house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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