PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

4.9 / 5.0

Outstanding(21 Ratings)

House in Orleans, MA

10 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsKitchen or Kitchenette, Air conditioner, Internet / Wifi and more

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

We have Wed June 18- Friday July 11 now open due to a cancellation. We are happy to work with you to find the length of stay and pricing that works for you. This is the only time open in 2025 - otherwise booked May - October.

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

Amenities

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Laundry

Balcony or Patio

Dishwasher

Wheelchair accessible

Family friendly

Map of Orleans, MA

Nearby attractions

Heritage Museums & Gardens

27.3 mi

Nauset Lighthouse

8.6 mi

John F. Kennedy Memorial

16.8 mi

Bourne Scenic Park

31.5 mi

$$$$

PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

$$$$

4.9 / 5.0

Outstanding(21 Ratings)

House in Orleans, MA

10 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsKitchen or Kitchenette, Air conditioner, Internet / Wifi and more

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

Amenities

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Laundry

Balcony or Patio

Dishwasher

Wheelchair accessible

Family friendly

Map of Orleans, MA

Nearby attractions

Heritage Museums & Gardens

27.3 mi

Nauset Lighthouse

8.6 mi

John F. Kennedy Memorial

16.8 mi

Bourne Scenic Park

31.5 mi

Ratings and reviews

4.9 / 5.0

Outstanding(21 Ratings)

Summary 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

4.0 / 5.0

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!

5.0 / 5.0

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.

5.0 / 5.0

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.

5.0 / 5.0

Aug 2021

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!

5.0 / 5.0

Jul 2021

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!

5.0 / 5.0

Dec 2020

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.

5.0 / 5.0

Sep 2020

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.

5.0 / 5.0

Jul 2020

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.

5.0 / 5.0

Sep 2019

Peaceful.

5.0 / 5.0

Aug 2019

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.

FAQs

How much does this house cost compared to others in Orleans?

The average price for a rental in Orleans is $401 per night. This rental is $718 above the average.

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 10 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and laundry.

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5.0 / 5.0

Outstanding(44 Ratings)

Close to beaches - Private Yard - 4 bed, 3 baths on 3 Levels!

House

in Harwich

10 guests · 5 bedrooms · 4 baths

Garden · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Orleans at Close to beaches - Private Yard - 4 bed, 3 baths on 3 Levels! for $1,210 for your next trip.

$$$$

PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

House in Orleans, MA

Reasons to book

About this house rental

Amenities

Map of Orleans, MA

Nearby attractions

PRIVATE WATERFRONT on Pleasant Bay. Perfect for families

House in Orleans, MA

Reasons to book

About this house rental

Amenities

Map of Orleans, MA

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in Orleans?

Is parking included with this house?

Is there a pool at this house?

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

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

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