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Enchanting Waterfront Summer Escape on Pleasant Bay

Photo gallery for Enchanting Waterfront Summer Escape on Pleasant Bay

Sunrise from the deck. There is a power awning for shade.
The living room with panoramic views
Exterior
Sunrise from the deck looking south so this is a reflective sunset.
Main floor master bedroom with full bath and Jacuzzi tub.

Reviews

9.6 out of 10
Exceptional
4 bedrooms4+ bathroomsSleeps 62700 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Orleans, MA
  • Place, Pilgrim Lake
    ‪11 min walk‬
  • Place, Cape Cod Beaches
    ‪7 min drive‬
  • Place, Skaket Beach
    ‪11 min drive‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪31 min drive‬

Rooms & beds

4 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Single Bed and 1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

4 bathrooms, 1 half bathroom

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet

Master Bath 1

Bathtub · Toilet · Shower only · Jetted bathtub

Master Bath 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Enchanting Waterfront Summer Escape on Pleasant Bay

Beautiful Pleasant Bay waterfront vacation home with 180 degree unobstructed views of the Pleasant Bay estuary. This vacation home is about light-filled rooms virtually all with a view of the water, kayaking, canoeing, sailing, fishing and more: a most unique, charming, enchanting yet substantial home in the Mayflower Point area.

Waterfront with deep water access, gentle path down to the sandy beach, first floor master suite, living room, open kitchen and dining, family room, all with water views; 3 decks from which to choose your sun or shade exposure. 4 bedrooms and 4.5 baths.

Main floor master bedroom with a king bed, second floor master has a queen size bed, a single bed and private bath. A third bedroom has a Queen size bed and bath down the hall. All three of these bedrooms have water views.

The kitchen, located in the center of the house, is perfect for entertaining. Plenty of counter space and two sinks allow all guests to participate in preparing meals.

A separate rec room provides recreation space for playing Pool, watching movies or playing games. The rec room is in a separate building and has a full bath and may be used for overflow sleeping if needed.

Of course all of the basics are provided including a grill and plenty of outdoor furniture. There are two kayaks at the house that you're welcome to use. Linens and towels are included and provided through a professional linen service.

The house is situated in a quiet rural neighborhood and is the perfect setting for a relaxing, waterfront experience.
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: 30
Check out before 10:00 AM
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Children

Adults only
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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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number C0113682240

We should mention

A car is required for transport to and from this property

About the area

Orleans

Located in Orleans, this holiday home is in the city centre and on the beach. The area's natural beauty can be seen at Cape Cod National Seashore and Cape Cod Beaches. Travelling with kids? Consider Orleans Bowling Center and Cape Escape Adventure Golf. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in OrleansOpens in a new window
Map
Orleans, MA

What's nearby

  • Pilgrim Lake - 11 min walk - 1.0 km
  • Cape Cod Beaches - 7 min drive - 2.9 km
  • Skaket Beach - 11 min drive - 6.4 km
  • Nauset Beach - 11 min drive - 6.1 km
  • Cape Cod National Seashore - 13 min drive - 10.9 km

Getting around

  • Hyannis Transportation Center - 35 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 33 min drive

Restaurants

  • ‪Wendy's - ‬7 min drive
  • ‪Hot Chocolate Sparrow - ‬6 min drive
  • ‪Dunkin' - ‬6 min drive
  • ‪Hog Island Beer Co. - ‬8 min drive
  • ‪Town Cove Tap House - ‬6 min drive

Frequently asked questions

Is Enchanting Waterfront Summer Escape on Pleasant Bay pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Enchanting Waterfront Summer Escape on Pleasant Bay?

As of 24 Mar 2026, prices found for a 1-night stay for 2 adults at Enchanting Waterfront Summer Escape on Pleasant Bay on 24 Mar 2026 start from £1,049, 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.

How much is parking at Enchanting Waterfront Summer Escape on Pleasant Bay?

On-site parking is available at the property.

What time is check-in at Enchanting Waterfront Summer Escape on Pleasant Bay?

Check-in begins at 4:00 PM.

What time is check-out at Enchanting Waterfront Summer Escape on Pleasant Bay?

Checkout is at 10:00 AM.

Where is Enchanting Waterfront Summer Escape on Pleasant Bay located?

Located in Orleans, this beachfront holiday home is in the city centre, 2.7 mi (4.3 km) from Orleans Bowling Center, and 3.1 mi (5 km) from Cape Escape Adventure Golf. Cape Cod Beaches and Cape Cod National Seashore are also within 6 miles (10 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 24 out of 28 reviews
Rating 8 - Good. 2 out of 28 reviews
Rating 6 - Okay. 1 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 1 out of 28 reviews

9.4/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Heidi M.

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

Pleasant time on Pleasant Bay

We had a great vacation in Orleans. The property is beautiful.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Pamela K.

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

Great house!

Xxx
Stayed 14 nights in Jul 2024
Verified

10/10 Excellent

Bonnie C.

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

Orleans house

We had a fantastic stay at this property in Orleans. It was a beautiful home on a bay with windows and decks everywhere. Was very well stocked and Very comfortable for six adults. Also centrally located to Nauset Beach, the rail trail and the towns of Orleans, Chatham and Provincetown. And while close to lots of great restaurants the property was so beautiful we ate in many nights. The host was very communicative and helpful. We thoroughly enjoyed our stay and can’t wait to return.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

marilyn v.

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

Beautiful home you want want to leave!

House is beautiful with Incredible views. Location is wonderful. Pool room, kayaks etc. Only negative is that the stairs make it a tough if you have someone who has difficulty ambulating. But otherwise we loved it....if they allowed service animals we'd be there each year@
Stayed 14 nights in Aug 2021
Verified

10/10 Excellent

Diana S.

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

Memorable family time together

Extraordinary views of Pleasant Bay any time of day or night. Opening my eyes to the sunrise over the calm morning water was a special surprise. We were three couples plus two grandchildren, ages 5 and 2, and the bedroom setup, well appointed kitchen, multiple spaces for being together or apart made for a relaxed and wonderful time away, yet together. The game room with pool table was especially fun for after dinner competition! Located close to Orleans Center and shopping, restaurants, groceries. We enjoyed both the calm waters and low tide flats of the bay at Skaket Beach and the waves at Nauset Beach on the ocean side. Would highly recommend! Owners were very responsive to any questions we had.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Mike B.

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

Orleans seaside vacation

Great house in a location we really enjoyed. The views are amazing and it is very relaxing to just sit and watch the boats go by. The 2 paddle boards were a nice escape and my kids fished off the shore below the house. We were close to town and Nausett and really just about everything we wanted to access on the Cape. The house itself is great. We used it all from the hammock, to the porch, to the BBQ, and the TV/entertainment room. The kitchen is good for cooking and has everything. There is even a good selection of oils, spices, and the like. The owners were very communicative / helpful and their welcome book and binder had it all. Only negative was that the house did not come with sheets and towels. We brought our own but for the price paid and the amount we pay to clean on top of that, they should be included as they are throughout the world: pandemic, endemic or no situation at all. That was a first for me. Still, we would definitely come back.
Stayed 7 nights in Aug 2022
Verified

6/10 Okay

Terry P.

Liked: Cleanliness, check-in, communication, location

Access

There were exceptional views but it should be highlighted that the house is difficult to get to since you have to navigate uneven stairs which is hard when you are trying to load and unload luggage
Stayed 7 nights in Sep 2021
Verified

8/10 Good

Carol P.

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

Property review

The views from the house are stunning. The deck is a great place to sit and relax and watch the bay with all the wildlife and boat activity. It was really nice to have the kayaks as it allowed us to explore all the coves and inlets of the bay.
Stayed 14 nights in Aug 2021
Verified

10/10 Excellent

Rochelle C.

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

Beautiful house

This was a baeutiful house in a beautiful location. Everything about the week was amazing!!
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Katerina T.

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

Peaceful week.

We had such a relaxing, perfect week staying in this beautiful house. It was everything and more then we expected. Clean, peaceful and private. No need to really go anywhere simply because we enjoyed the property so much. The house is full of light. Every morning we were witnessing a beautiful sunrise and had coffee on the porch with our 2 month old daughter next to us. My mom, my nanny and our seven year old all came on this trip too. We were all together yet had enough room to experience privacy. My husband and I both agree that we would come back to this beautiful house anytime. Highly recommend!
Stayed 7 nights in Oct 2020
Verified

2/10 Terrible

Ginger K.

Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy

Poorly maintained house, untrustworthy owner

The single best thing about this house is the location. The view is as shown in the listing, and the house is in a pretty, wooded neighborhood. The kitchen is generally well stocked; and the TV in the den is large. Other things about the listing are misleading. The path from the driveway to the front door (main level) of the house is not shown. Instead, only the path up to a second-floor bedroom is shown. The main level of the house is actually a full level *below* the driveway, and the path to it comprises a long flight of steep, narrow, uneven stone-and-wood steps. The owner knew that we were planning to vacation with my 101-year-old mother, who had trouble walking, but she did not mention that there was no way my mother could get into or out of the house without climbing a full flight of stairs. The two bedrooms downstairs are cramped, unpleasant, and clearly basement spaces (although the larger of the two rooms does have a door that leads outside). From the outset, there were numerous other problems with this house that suggested it is not checked out adequately between rentals. • There were three wooden cutting boards that were each cracked in half • Roasting pan had been put away wet and was covered in rust • Several very dirty dishes (food dirt) were stacked among the clean ones • Kitchen shelves were dirty • The coffee maker needed cleaning • There were not even four matching wineglasses • Small refrigerator in the kitchen desperately needed defrosting • There were missing ceiling bulbs in the kitchen and dining area, and the only two lamps in the living room had 3-way lamps but the bulbs had only the dimmest wattage working. Even with new bulbs, the living room is very dark at night • The master bathroom has three fluorescent fixtures over the sink. Only one of these was working. The owner got the smaller, middle fixture to work, but with a very loud buzzing. He had known that the third fixture was broken but had not had it fixed while the house was vacant • The jacuzzi bathtub did not work There were high winds one day, and the owner removed all but 3 of the outdoor deck chairs. He never put them back. The wifi service does not extend far beyond the den. We couldn't use wifi in the living room, master bedroom, or deck. When my mother became suddenly hospitalized, we had to leave early. The owner kindly promised a partial refund of a certain amount but only ever refunded half of this written promise. He was very unpleasant to deal with.
Stayed 21 nights in Sep 2020
Verified

10/10 Excellent

Jennifer E.

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

Perfect vacation home

We had such a wonderful vacation week. The house was perfect. Extremely clean. The owners went above and beyond on cleanliness. The fully stocked kitchen and open and bright living room made the time spent inside just as enjoyable as outside which is a hard task with the view this house has. Morning coffee on the deck as boats passed by was breathtaking. We enjoyed kayaking and sitting on the beach relaxing. We will definitely rent again. It was perfect. Thank you!
Stayed 8 nights in Aug 2020
Verified

10/10 Excellent

Meredith R.

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

Late summer escape

We had a wonderful, peaceful stay at this lovely East Orleans house. While there were only two of us, the house is set up well for an extended family or multiple families. The house has wonderful outdoor space and water access for kayaking (we swam right in front of the house as well though there is boat traffic to be mindful of). The hosts made check-in and check-out very easy. All in all a lovely spot to enjoy the last few days of summer.
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Jeremy F.

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

Perfect getaway during the pandemic

It was wonderful waking up to beautiful views every morning. The home is somewhat isolated, but that was perfect given our health concerns during the COVID pandemic. The home Is spacious and comfortable and has everything we needed.
Stayed 14 nights in Aug 2020
Verified

10/10 Excellent

Glenn M.

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

Fun Cape Reunion

We very much enjoyed our stay, and Cheryl was an attentive host. Excellent location, wonderful house, many amenities and thoughtful touches. We would go back.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Verified traveller

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

Highly recommend!

We chose this property as the place to take our children and grandchildren to celebrate our 50th wedding anniversary. It worked out perfectly for our multigenerational group. We enjoyed kayaking, cooking, eating seafood in local restaurants, visiting nearby beaches, biking on the Cape Cod rails to trails path, and playing games in the evening. The house has everything you need and lots of nooks and crannies where people can cozy up with a book, watch tv, or lounge on the hammock. Spectacular water views await at every turn. The owners were very helpful but unobtrusive. We had a wonderful time and highly recommend this rental for your group.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Laura D.

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

The house was amazing and we had a great week. The view of the bay was spectacular.

We had a great week and the property owners were terrific.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

katie p.

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

peaceful paradise

We stayed here with our extended family and couldn't have been happier. The views of the water and multi-tiered porch was amazing for big family dinners while the cousins ran around in the back yard. There was plenty of space for folks to gather an the open kitchen was great for lots of people to help with meal prep. We got lots of use out of the 4 kayaks. And Rich gave us some great tips on where to go -- like swimming in Crystal lake down the street. We had a wonderful time and can't wait to come back.
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Dori J.

Perfect spot for a friends' reunion

What a wonderful find. We were looking for a place for four couples to share for our annual college mini reunion. This was perfect. We went in October so the Cape (Orleans) was lovely and quiet, and the house showed off the Fall weather just perfectly. The house is beautiful (as the pictures show), there is a 270-degree view of the water and inlet, the house is well-furnished and well-supplied with everything you would want for entertainment if you choose to stay inside (huge TV; wi-fi, "Alexa," lovely linens, W/D, etc.). But why stay inside? Cape Cod National Seashore is nearby, Chatham and Orleans are lovely, Martha's Vineyard and Nantucket are just ferry rides away, and the owners provide kayaks to explore the inlet. It was perfect for us. Three couples stayed in the main house; the fourth stayed in the Rec Room which has its own shower and bath. It was a lovely experience!
Stayed 4 nights in Oct 2018
Verified

10/10 Excellent

Terri P.

Most Special Place....

To say that this home is perfect is an understatement. Not only is the house in an amazing location, with a perfect view, but it is so comfortable (linens, beds, etc.). We were a rather large group and had more than enough space for each family. We didn't have to worry about toilet paper, cleaning/laundry products, paper towels etc. Everything was there for us. I have yet to stay in a VRBO that is this generous and thoughful! Owners are amazing - everything we needed they were ready and willing to help! Many thanks for a wonderful week.
Stayed 7 nights in Jul 2018
Verified

10/10 Excellent

Deb S.

Fabulous home, lovely location

Beautiful house, wonderful hosts! Loved watching the boats go by and the seals in the morning. The house was very well equipped, spacious and clean. Would highly recommend it!
Stayed 7 nights in Aug 2018
Verified

10/10 Excellent

Mary P.

Amazing home

This home is beautifully furnished, amazing views and extremely spacious. The owners left a lovely basket of wine and cheese upon our arrival and stopped by later in the day to make sure we didn’t need anything. Would highly recommend!
Stayed 7 nights in Jun 2018
Archival

10/10 Excellent

Joe B.

Great Location

Incredible views. Lovely place. Landlords very helpful and friendly.
Stayed 7 nights in Aug 2017
Archival

10/10 Excellent

Neil B.

Fantastic property in idyllic location

We spent a terrific couple of weeks at this Orleans property, close enough to the beaches both sides of the Cape, but remote enough to be your own private getaway. The house was excellent, fully stocked and no complaints. The water views amazing, and Cheryl & Rich were thoughtful hosts -- even taking us on their boat for a trip on Pleasant Bay. I can't recommend this highly enough. Thanks again!
Stayed 14 nights in Aug 2017
Archival

10/10 Excellent

Thomas F.

Perfect venue and great hosts

Cheryl and Richard went above and beyond to make sure that we had everything that we needed for a great stay at the Cape. The house itself was incredible. 270 degree water views. It feels very private, but yet close to town. Highly recommended.
Stayed 7 nights in Jul 2017

About the host

Hosted by Cheryl Nadler

Host profile image

Why they chose this property

The cottage is situation in a quiet rural neighborhood and is the perfect getaway for relaxing cape cod waterfront experience. It is not an appropriate location for large or loud groups.

Languages:

English
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