House in Orleans, MA
19 guests · 9 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
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.
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'.
.
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.
Amenities at Waterfront. Private beach. Pool. Estate has it all!!
Free WiFi/internet
Air conditioning
Pool
Non-smoking
TV
Wheelchair accessible
Coffee/tea maker
Refridgerator
Kitchen
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
No pets allowed
Garden
Oven
Stove
Laundry services
Fireplace
Bath or shower
Ironing facilities
Towels
Hairdryer
Map of Orleans, MA
Ratings and reviews
Summary of reviewsThe Winslow estate is perfect for family gatherings, weddings, and special events. The property offers stunning views, spacious accommodations, and attentive hosts. Highly recommended for unforgettable experiences.
10.0 / 10.0Outstanding·Aug 2024
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!!
10.0 / 10.0Outstanding·Jul 2022
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.
10.0 / 10.0Outstanding·Aug 2020
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.👍
6.0 / 10.0Average·Sep 2025
The location, privacy, views, and grounds are outstanding. The house is large and rustic, with recently remodeled bathrooms but other areas that show its age. Since our stay, the listing has been updated with a floor plan. After booking a 9-bedroom home we were surprised that two are enclosed lofts only accessible through adjoining rooms. This was an issue for our group.All 11 split A/C units had mold. The host responded quickly and had them cleaned during our stay. Disruptive for us, but good for future guests. There were ants and mice in the kitchen. The main refrigerator was broken. (If a house comes with a note in the kitchen explaining how refrigerators cool and with instructions not to adjust the temperature, it’s clear there is a known issue.) Per the instructions we spent the first couple of days waiting for the fridge to work. We ended up tossing our perishables and moving everything to the second fridge.The house didn’t feel clean: bathmats appeared vacuumed but not laundered, shower curtain and tub mat were stained, the toaster had not been emptied, and we found a pair of briefs on a lamp when we checked in. Upholstery and carpeting felt grimy, radiators were dusty, and the laundry room was cluttered and unkempt.That said, we recognize the challenges of maintaining an aging seaside estate. The host, Ginger, was gracious, responded promptly to issues, and provided a partial refund. With improvements, this could be an exceptional property.
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Top rated by guests
10.0Outstanding
(34 Ratings)
The Winslow estate is perfect for family gatherings, weddings, and special events. The property offers stunning views, spacious accommodations, and attentive hosts. Highly recommended for unforgettable experiences.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
