Entire home
PRIVATE WATERFRONT on Pleasant Bay. Perfect for families
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Reviews
10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 10
Popular amenities
Explore the area

Orleans, MA
- Place, Cape Cod Beaches5 min walk
- Place, Cape Cod National Seashore16 min drive
- Place, Mayflower Beach28 min drive
- Airport, Hyannis, MA (HYA-Barnstable Municipal)29 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom
2 Single Beds
Bedroom
2 Single Beds
Bedroom
2 Single Beds
Bedroom
1 Queen Bed
Bedroom
1 Queen Bed
3 bathrooms
Bathroom
Toilet · Shower only
Bathroom
Outdoor shower
Bathroom
Bathtub or shower · Toilet
Bathroom
Bathtub or shower · Toilet
Spaces
Deck or patio
Outdoor shower
Kitchen
About this property
PRIVATE WATERFRONT on Pleasant Bay. Perfect for families
Waterfront home with gorgeous views across Pleasant Bay. Watch the boats sail by from your sunny deck & soak in the breathtaking views across Pleasant Bay. Enjoy swimming, kayaking, paddleboarding from your own 100'+ PRIVATE waterfront.
Dig clams, collect shells, wander along the shore. Supremely quiet & private estate location, great area for walking, jogging, and bike riding. Multiple nature walks/conservation areas nearby for walks.
Newly redecorated, upscale, light & airy. Central A/C, wifi and several flat screen TV's make living easy. Two master bedrooms en suite. The five bedrooms are really five bedrooms - not common rooms that become bedrooms at night. There are no sofa beds, futons, trundle beds, or cots. Everyone has a personal and private space. Private enclosed outdoor shower.
The waterfront area has a mixture of sand, pebbles, rocks and grass. The pictures shown are accurate of our 'beach'. Jacknife Point in Chatham (free parking) is a few miles away with a wide expanse of sandy beach -see pictures. ;;
Beach, bed and bath linens included for weekly rentals.
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.
Orleans is known for the waves at Nauset Beach and the sand bars/warm tidal pools and setting sun at Skaket Beach. Chatham shopping is a short drive away. A most quiet, pastoral estate setting for the waterfront property, yet you are a short driveway from all the amenities Orleans and Chatham have to offer with shopping, restaurants and summer activities.
Amazing property! This very special property has been owned by the same family on the shores of Pleasant Bay for over 100 years. The Bay House was built in the 1950's, added on to in the 1980's and totally redone in the 1990's.
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. The private beach is private just for you - not the 10 houses in the neighborhood. It is reached by a pathway down the bluff in front of the house. You can sit on the beach and listen for children napping in the home above - no more running back and forth to public parking lots with little ones.
Pleasant Bay with its gradual bottom and warm water is lovely for swimming, floating on rafts, windsurfing, sailing, kayaking, and long walks along the shore.
Location: South Orleans is ideally located at the elbow of cape cod, equal distance between Orleans and Chatham - two if the prettiest towns on Cape Cod. Chatham ('Nantucket without the drama of getting there') has terrific shops and restaurants along its Main Street and some lovely beaches. Orleans also has great shopping and restaurants and has world famous Nauset Beach for waves and Skaket Beach, everyone's favorite for little ones with warm water and sand bars going out for miles. Provincetown to the north is great fun for a day and Hyannis to the west has a lot to offer as well.
See a floor plan at our web site winslowestates.com
Dig clams, collect shells, wander along the shore. Supremely quiet & private estate location, great area for walking, jogging, and bike riding. Multiple nature walks/conservation areas nearby for walks.
Newly redecorated, upscale, light & airy. Central A/C, wifi and several flat screen TV's make living easy. Two master bedrooms en suite. The five bedrooms are really five bedrooms - not common rooms that become bedrooms at night. There are no sofa beds, futons, trundle beds, or cots. Everyone has a personal and private space. Private enclosed outdoor shower.
The waterfront area has a mixture of sand, pebbles, rocks and grass. The pictures shown are accurate of our 'beach'. Jacknife Point in Chatham (free parking) is a few miles away with a wide expanse of sandy beach -see pictures. ;;
Beach, bed and bath linens included for weekly rentals.
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.
Orleans is known for the waves at Nauset Beach and the sand bars/warm tidal pools and setting sun at Skaket Beach. Chatham shopping is a short drive away. A most quiet, pastoral estate setting for the waterfront property, yet you are a short driveway from all the amenities Orleans and Chatham have to offer with shopping, restaurants and summer activities.
Amazing property! This very special property has been owned by the same family on the shores of Pleasant Bay for over 100 years. The Bay House was built in the 1950's, added on to in the 1980's and totally redone in the 1990's.
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. The private beach is private just for you - not the 10 houses in the neighborhood. It is reached by a pathway down the bluff in front of the house. You can sit on the beach and listen for children napping in the home above - no more running back and forth to public parking lots with little ones.
Pleasant Bay with its gradual bottom and warm water is lovely for swimming, floating on rafts, windsurfing, sailing, kayaking, and long walks along the shore.
Location: South Orleans is ideally located at the elbow of cape cod, equal distance between Orleans and Chatham - two if the prettiest towns on Cape Cod. Chatham ('Nantucket without the drama of getting there') has terrific shops and restaurants along its Main Street and some lovely beaches. Orleans also has great shopping and restaurants and has world famous Nauset Beach for waves and Skaket Beach, everyone's favorite for little ones with warm water and sand bars going out for miles. Provincetown to the north is great fun for a day and Hyannis to the west has a lot to offer as well.
See a floor plan at our web site winslowestates.com
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- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (83 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number C0035962240
About the area
Orleans
Located on the beach, this holiday home is in South Orleans, a neighbourhood in Orleans. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Orleans Bowling Center and Cape Escape Adventure Golf are also worth visiting. Discover the area's water adventures with waterskiing and water tubing nearby, or enjoy the great outdoors with mountain biking and cycling.

Orleans, MA
What's nearby
- Cape Cod Beaches - 5 min walk - 0.4 km
- Chatham Lighthouse - 15 min drive - 14.4 km
- Cape Cod National Seashore - 16 min drive - 14.7 km
- Mayflower Beach - 28 min drive - 31.1 km
- Hyannis Harbor - 29 min drive - 36.2 km
Getting around
Restaurants
- Dunkin' - 11 min drive
- Hog Island Beer Co. - 11 min drive
- Three Fins Coffee House & Cacao Factory - 12 min drive
- Corner Store - 11 min drive
- 400 East - 11 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
1 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Aug 2025
Verified
10/10 Excellent
William and Sandra P.
12 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Family Rental
William and Sandra P.
Stayed 6 nights in Aug 2022
Verified
8/10 Good
Ellen S.
17 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Winslow Estates
Ellen S.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Danielle M.
31 May, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Marvelous stay!
Danielle M.
Stayed 3 nights in May 2022
Verified
10/10 Excellent
Verified traveller
30 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
A gem of a property!
Verified traveller
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Norma L.
18 Jul, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
The view…the view
Norma L.
Stayed 14 nights in Jul 2021
Verified
10/10 Excellent
Dyana S.
5 Dec, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing views, private beach
Dyana S.
Stayed 4 nights in Nov 2020
Verified
10/10 Excellent
Sonalee A.
21 Sept, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous view of the water!!
Sonalee A.
Stayed 5 nights in Sep 2020
Verified
10/10 Excellent
Natalie H.
28 Jul, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, private beach get away
Natalie H.
Verified
10/10 Excellent
Michael M.
4 Sept, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet place
Michael M.
Stayed 7 nights in Aug 2019
Verified
10/10 Excellent
Kirsten B.
12 Aug, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Bay House!
Kirsten B.
Stayed 7 nights in Aug 2019
Verified
10/10 Excellent
S G.
15 Jul, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful
S G.
Stayed 7 nights in Jul 2019
Archival
10/10 Excellent
marci d.
4 Aug, 2016
Great time was had by all
marci d.
Archival
10/10 Excellent
Kayla R.
21 Jun, 2016
Beautiful, fun, relaxing
Kayla R.
Archival
10/10 Excellent
Gaurav F.
14 Sept, 2015
Beautiful Property!
Gaurav F.
Archival
10/10 Excellent
Patricia G.
3 Jun, 2015
A beautiful venue for our niece's wedding!
Patricia G.
Archival
10/10 Excellent
cathleent T.
11 Sept, 2014
We WILL be back!!!!
cathleent T.
Archival
10/10 Excellent
hannah b.
11 Oct, 2013
An ideal cape getaway!
hannah b.
Archival
10/10 Excellent
Susan R.
3 Aug, 2012
Bay House Rental
Susan R.
Archival
10/10 Excellent
Donna L.
20 Jul, 2011
Loved the Bay House!
Donna L.
Archival
10/10 Excellent
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15 May, 2010
Wonderful Place!
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Archival
10/10 Excellent
26 May, 2009
Amazing location
About the host
Hosted by Ken Winslow
Why they chose this property
Cancellation Policy - all payments returned upon our ability to re-rent the property for the same time period for the same amount.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
What makes this property unique
Cancellation Policy - all payments returned upon our ability to re-rent the property for the same time period for the same amount.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
Rental period in the summer is Friday to Friday to allow you to have friends and family visit for a FULL weekend. It also skips all the terrible traffic tie ups on Saturday and Sunday.
Languages:
English
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