
Vacation rentals in Pleasant Bay
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Pleasant Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Pleasant Bay vacation rentals
Other great vacation rentals in Pleasant Bay
Guest favorite

Private room in Orleans
4.93 out of 5 average rating, 190 reviewsHillside Cape Getaway
AbigailRating, 5 stars3 weeks ago
Definitely will be there again! Kim is amazing, her home is so peaceful and she was so kind! Honestly this is the perfect place for a quiet place to read and relax!

Condo in Chatham
4.79 out of 5 average rating, 81 reviewsLavish 1BR | Balcony | Washer/Dryer
BriRating, 5 stars1 month ago
You cannot beat the location, you’re right in the center of town but with the benefit of a parking spot. The place itself was clean, new and well designed. Looks just like the photos!
Top guest favorite

Private room in Orleans
4.88 out of 5 average rating, 181 reviewsCozy Corner!
PaulRating, 5 stars9 months ago
Great 2-night stay for a charity event. Perfect location and a super host!
Guest favorite

Apartment in Chatham
5 out of 5 average rating, 5 reviewsChatham Studio- .5 mile to beach
RogerRating, 5 stars8 months ago
A great stay to base out of to explore Chatham and lower Cape. Tom was very helpful and responsive.

Apartment in Brewster
5 out of 5 average rating, 3 reviewsBright and Peaceful Studio
AlexisRating, 5 stars3 weeks ago
Nestled in a beautiful and private neighborhood in Brewster, this Airbnb was the perfect weekend getaway. The yard was spacious and great for our dog to run around to play fetch in and sun on the deck. We loved mornings out on the deck table listening and spotting birds. The unit was clean and cozy. There’s ample daylight in the unit and lots of windows. The fold down Murphy bed was straight forward to set up. The kitchen was stocked with the essentials. The water pressure in the bathroom shower was great and the water heated up fast. The hosts are responsive and friendly. They have amenities like bikes and paddle boards that we didn’t end up utilizing. Inside the unit was a great little binder of local recommendations and we tried a handful of them and ate lots of great food.
Top guest favorite

Hotel room in Chatham
4.96 out of 5 average rating, 179 reviewsMain Suite - Chatham Guest Rooms
PatriciaRating, 5 stars2 weeks ago
What a fabulous stay in Bob’s beautiful apartment! This was my second visit, and I wouldn’t stay anywhere else. The spacious apartment is immaculately clean and very well appointed - Bob has thought of everything, and it is full of lovely touches. Very comfortable bed, cozy living room with a great library, well-equipped modern kitchen, a full-sized washer and dryer, and a wonderful bathroom with lots of storage. Bob is a very responsive host, and this charming accommodation gets my very highest recommendation!!
Guest favorite

Private room in Eastham
4.92 out of 5 average rating, 103 reviewsKnowles Farm B&B, Photo Room
TaylorRating, 5 stars3 weeks ago
A beautiful home in a great location on the cape, also near walking trails and amazing nature! Our room and the space designated for guests is awesome. Sarah was a great host and has fostered a wonderful community through her BnB.
Guest favorite

Private room in Orleans
4.89 out of 5 average rating, 114 reviewsOrleans Apartment and 12 Forest Way
BillRating, 5 stars9 months ago
Our family loved our stay at Bob’s place. Bob and Joyce were so welcoming, and their space was as promised and more-clean, spacious, quiet, and conveniently located. Our only regret is that we couldn’t stay longer.
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Coast Guard Beach
- Owen Park Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- Oyster Harbors Beach
- White Horse Beach
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Peggotty Beach
- Forest Beach
- Lighthouse Beach
- Corporation Beach
- Linnell Landing Beach