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PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

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

View to Pleasant Bay from the deck
Beautiful view across Pleasant Bay
Lots of seating for fun on the deck.
View from the chaises
view down to the beach

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Orleans, MA
  • Place, Cape Cod Beaches
    ‪5 min walk‬
  • Place, Chatham Fish Pier
    ‪13 min drive‬
  • Place, Chatham Lighthouse
    ‪15 min drive‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪29 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom

2 Twin Beds

Bedroom

2 Twin Beds

Bedroom

2 Twin 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
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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
Onsite 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Property Registration Number C0035962240

About the neighborhood

Orleans

Located on the beach, this vacation home is in South Orleans, a neighborhood 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 water skiing and water tubing nearby, or enjoy the great outdoors with mountain biking and cycling.
View more Vacation Homes in OrleansOpens in a new window
Map
Orleans, MA

What's nearby

  • Cape Cod Beaches - 5 min walk - 0.4 km
  • Chatham Fish Pier - 13 min drive - 13.4 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

Getting around

  • Hyannis Transportation Center - 31 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 32 min drive

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

Is PRIVATE WATERFRONT on Pleasant Bay. Perfect for families pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families?

As of Apr 2, 2026, prices found for a 1-night stay for 2 adults at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families on May 2, 2026 start from $1,000, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families?

Check-in begins at 4:00 PM.

What time is check-out at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families?

Check-out is at 11:00 AM.

Where is PRIVATE WATERFRONT on Pleasant Bay. Perfect for families located?

Nestled on the beach, this South Orleans vacation home is within 3 mi (5 km) of Cape Cod Beaches, Captain's Cove Golf Course, and Nickerson State Park. Rock Harbor Beach and Skaket Beach are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 22 reviews
Rating 8 - Good. 1 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views and very nice owners nearby who were responsive and helpful.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

William and Sandra P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Rental

We were celebrating our 50th anniversary and my husband's upcoming 80th birthday. We needed a space for 10 family members that was quiet and had waterfront but convenient to everything we needed. This was a perfect spot for our age ranges. We had grandsons ages 8 and 11 and young adult parents and of course we "oldies but goodies". Everyone was happy. Beautiful property.
Stayed 6 nights in Aug 2022
Verified

8/10 Good

Ellen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winslow Estates

For the money I would upgrade the bath towels (very rough on skin) AC was not strong enough to accommodate the entire house and there was not a beach to play or swim as advertised. The rough terrain made it hard to walk to the water, there was no sand to play or sit and very rocky. A beach area would have been nice!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Danielle M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Marvelous stay!

We had a lovely long weekend at Ginger and Ken’s home in Orleans. The views overlooking the bay were truly out of this world. The home is clean, spacious and surrounding neighborhood quiet and peaceful. There are numerous nature trails near the propriety great for running or a nice leisurely stroll. We easily made day trips to Provincetown and Wellfleet for biking, hikes and trips to the beach. If you’re looking for a comfortable home to share with family and friends - look no further! We loved every minute of our stay.
Stayed 3 nights in May 2022
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

A gem of a property!

My family had a wonderful time. The house was clean, spacious enough that our party of 8 felt very comfortable, and location location location! The older members of our group enjoyed sitting on the back porch reading and taking in the amazing views of the water... and the younger ones loved going down to the water to swim, kayak, and discover the many treasures along the shore! Ginger and Ken were very responsive and attentive hosts. We will definitely return!
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Norma L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The view…the view

Unfortunately during our two week stay we could have had better weather. However, the view almost made up for it!! Even with rain there is something about having your coffee looking at the water be it sunny, fog or rain 😁 First time our family stayed in Orleans and we really liked the location…ice cream shops everywhere FYI!! Ginger and Ken (our hosts) actually were our neighbors and were quick to respond to any question…thank you. Great house for a family vacation…a lot of space. Highly recommend!
Stayed 14 nights in Jul 2021
Verified

10/10 Excellent

Dyana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing views, private beach

We had a great stay for thanksgiving! Weather was beautiful and we got to enjoy the hiking trails right down the road and the peaceful private beach. House is a bit outdated (similar to most cape houses) but space was great for our family and it had all the amenities we needed. Owner was friendly and easy to communicate with. Would definitely stay again.
Stayed 4 nights in Nov 2020
Verified

10/10 Excellent

Sonalee A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous view of the water!!

This is a perfect property to share with friends and family. The views of the water are perfect from anywhere in the house. There is enough space for children to run around and build sandcastles on a private beach. The house was very well equipped including things for beach trips. The kitchen was renovated and had an outdoor grill. Ginger and Ken were wonderful hosts. Will recommend this property.
Stayed 5 nights in Sep 2020
Verified

10/10 Excellent

Natalie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, private beach get away

Our stay at the Pleasant Bay home was wonderful. We had 8 family members that stayed, but 2-4 that would take day trips to join us for a day. As we are still a bit concerned about COVID- having the private yard and beach area was perfect for our family. Additionally, when we arrived the home was spotless and it was clear that a thorough cleaning job had been done. We spent most of our days outside and there was ample seating to accommodate everyone. We only went in when it got dark, and the home had beautiful large spaces to accommodate our large group of 10 people for board games and socializing. We cooked in a lot and the house had everything we needed to prepare our meals. Overall, we very much enjoyed our stay and would highly recommend.
Verified

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet place

Peaceful.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Kirsten B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Bay House!

What a beautiful home and setting. The view of Pleasant Bay was exceptional and memorable. It was great to have our own little beach to launch kayaks or take a quick dip. Ken and Ginger were excellent hosts and very accessible. We will definitely be back next summer.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

S G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

We had a wonderful family reunion here. The view of Pleasant Bay is lovely, the little private beach is perfect for young children, the layout of the house works well, the kitchen is large enough for 3-4 people to cook together and the beds are comfortable. Ginger was responsive and gracious when had questions. The location is perfect. Easy to get to beaches on the National Seashore, to the grocery store, and to restaurants This was our first visit to Cape Cod...and the house made it a great visit to a beautiful place.
Stayed 7 nights in Jul 2019
Archival

10/10 Excellent

marci d.

Great time was had by all

We rented 2 homes in Orleans for our artistic group of women - writers and artists. This home is perfectly set up for vacationers with its bright sunny kitchen, a lovely dining room, private bedrooms and all that peace and quiet at the end of a country road. The views of the water were wonderful - from sunrise to sunset. Walking along the shore was fun for all with sand under our toes and interesting artifacts to discover and treasure. A memorable stay at a terrific property.
Archival

10/10 Excellent

Kayla R.

Beautiful, fun, relaxing

We rented this house for part of our wedding party. It has a great beach/cape cod feel. There are plenty of bedrooms and the outdoor deck is where we spent a lot of time hanging out. The property is immaculate and well-maintained. We can't wait to rent this house in the future.
Archival

10/10 Excellent

Gaurav F.

Beautiful Property!

We were very impressed with the property and the location. We hardly left the house and choose to takeout so we could enjoy dinner with beautiful views. The house was large as stated and we plan to visit again next year!
Archival

10/10 Excellent

Patricia G.

A beautiful venue for our niece's wedding!

Since our family is scattered across the country, it was great to be able to stay together in one location. Having the rehearsal dinner and reception (in a tent behind the main house) was awesome. The view was spectacular! An awesome introduction to the Cape for some of our family members.
Archival

10/10 Excellent

cathleent T.

We WILL be back!!!!

If you're on the fence about whether to rent the Bay House, I am here to tell you that the pictures don't do it justice. My family and friends (party of 9) arrived for a birthday celebration weekend and were awe-struck as we drove down the driveway towards this beautiful destination. The minute you arrive, you know you're in for something special. The bay can be seen through the glass front door, giving you just a hint of what awaits. The cottage-type furnishings and farmhouse dining room table are warm and inviting and yet, casually elegant. We were greeted by fresh flowers on the table and in the front hallway. We treated ourselves to dinner on the back deck while watching the sun set and the moon rise over the water. Everyone loved this house with its private beach and scenic views so much that we hated to leave. One word...BEAUTIFUL! Thank you Ken and Ginger, for a wonderful weekend and amazing memories! We WILL be back! Cathy T
Archival

10/10 Excellent

hannah b.

An ideal cape getaway!

What a treat to stay at the bay house for a cape weekend getaway! Saturday morning we woke up to a peaceful scene right on the bay with a great blue heron fishing next door and a seal swimming by! The house was very comfortable with a great kitchen to prepare the huge stripers we caught fishing with Cape Cod Charters (only 2 miles away.) The location was ideal for explorations around the cape. I would definitely come back here again.
Archival

10/10 Excellent

Susan R.

Bay House Rental

My husband’s family rented the Bay House for a week in June of 2012. Besides adults, there were 3 small children. Everyone had a great time. The house was spacious, and it allowed for a relaxed vacation time. The bonus was that it was close to a private beach right on Pleasant Bay, which was wonderful for the kids. The house was neat and clean, and the property was lovely. The owners were extremely helpful with any questions that came up. We were very pleased with the rental in every way.
Archival

10/10 Excellent

Donna L.

Loved the Bay House!

We had a family reunion at the bay house in July 2011. It was the perfect location! Beautiful views and very quiet. We were able to catch the Chatham fireworks across the bay, did some fishing, claming, and swiming all without leaving the comforts of the property. We wiould definately recommend the bay house for your vacation destination. We loved it!
Archival

10/10 Excellent

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Wonderful Place!

My family and I (including 3 small children) stayed in this home in June 2009. What a great place! Very spacious and open. We loved that the adult quarters are well separated from the children's quarters and being on the bay was priceless. My kids really enjoyed walking the grounds and looking for seashells. Although our weather wasn't the greatest we really enjoyed our stay. The owners were extremely easy to work with and even went out of their way to return a treasured teddy bear to us that my son had left behind by accident. I would highly recommend this property.
Archival

10/10 Excellent

Amazing location

Just returned from a long weekend stay here. This house is perfect! Cozy, yet spacious. Clean, well equipped, great view, quiet, peaceful. Room to spread out, yet plenty of space to be together. Hesitant to write a good review, because I want to be sure it's available for me to rent again! Thanks to the owners, who were wonderful to work with.

About the host

Hosted by Ken Winslow

Host profile image

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.

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.

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English
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