Entire home
PRIVATE WATERFRONT on Pleasant Bay. Perfect for families
Photo gallery for PRIVATE WATERFRONT on Pleasant Bay. Perfect for families





Reviews
10 out of 10
Exceptional
5 bedrooms 3 bathrooms Sleeps 10
Popular amenities
Explore the area

Orleans, MA
- Ocean Edge Golf Club14 min drive
- Chatham Fish Pier14 min drive
- Chatham Lighthouse17 min drive
- Hyannis, MA (HYA-Barnstable Municipal)33 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, paddelboarding 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 Chtaham (free parking) is a few miles away with a wide expance 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 whom 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 know 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 fro 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 Chtaham (free parking) is a few miles away with a wide expance 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 whom 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 know 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 fro 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
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Ocean view
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10.0 out of 10, (35 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 in Orleans, this holiday home is on the beach. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Orleans Bowling Center and Chatham Marconi Maritime Center are also worth visiting. Discover the area's water adventures with waterskiing and water tubing nearby, or enjoy the great outdoors with cycling and mountain biking.

Orleans, MA
What's nearby
- Nickerson State Park - 7 min drive - 4.3 km
- Skaket Beach - 13 min drive - 9.5 km
- Ocean Edge Golf Club - 14 min drive - 9.6 km
- Chatham Fish Pier - 14 min drive - 13.0 km
- Chatham Lighthouse - 17 min drive - 14.4 km
Getting around
Restaurants
- Three Fins Coffee House & Cacao Factory - 12 min drive
- Hog Island Beer Co. - 11 min drive
- Dunkin' - 11 min drive
- The Barley Neck Inn - 11 min drive
- Dunkin' - 11 min drive
Frequently asked questions
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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