PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

Top rated by guests
View to Pleasant Bay from the deck
Bright and sunny kitchen with corian counters
another kitchen photo
view from the second master bedroom with private patio
Beautiful view across Pleasant Bay
review stars
9.8Outstanding
(22 Ratings)
The property offers beautiful views of the water, a quiet location, spacious accommodation, and easy beach access.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.8 / 10.0
Outstanding(22 Ratings)

House in Orleans, MA

10 guests · 5 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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

Amenities at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

Air conditioning
Non-smoking
TV
Wheelchair accessible
Coffee/tea maker
Refridgerator
Kitchen
WiFi/Internet
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
No pets allowed
Oven
Stove
Laundry services
Fireplace
Bath or shower
Ironing facilities
Towels
Hairdryer

Map of Orleans, MA


Ratings and reviews

9.8 / 10.0
Outstanding(22 Ratings)
review starsSummary of reviews
The property offers beautiful views of the water, a quiet location, spacious accommodation, and easy beach access.
From real guest reviews summarized by AI
10.0 / 10.0Outstanding·Sep 2025
Beautiful views and very nice owners nearby who were responsive and helpful.
8.0 / 10.0Excellent·Aug 2022
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!
10.0 / 10.0Outstanding·Aug 2022
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.
10.0 / 10.0Outstanding·May 2022
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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at PRIVATE WATERFRONT on Pleasant Bay. Perfect for families?

We found 23 amenities for this rental. This includes air conditioning, non-smoking, tv, wheelchair accessible, and coffee/tea maker.


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