
Vacation rentals in Pleasant Bay
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Top-rated vacation rentals in Pleasant Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Pleasant Bay vacation rentals
Other great vacation rentals in Pleasant Bay
Top guest favorite

Cottage in East Orleans
4.96 out of 5 average rating, 133 reviewsDistiller’s Cottage Nauset Beach East Orleans, MA

Apartment in Orleans
4.57 out of 5 average rating, 168 reviewsModern Cape Apartment in Orleans, Private Entrance
Top guest favorite

Cottage in Chatham
4.97 out of 5 average rating, 257 reviewsCozy Cottage
Top guest favorite

Home in Chatham
4.97 out of 5 average rating, 146 reviewsThe Osprey Nest - Beach house with stunning views
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Home in Orleans
5 out of 5 average rating, 11 reviewsPetite Antique, location, location, location
Guest favorite

Home in Eastham
5 out of 5 average rating, 6 reviewsEastham Bungalow
Top guest favorite

Guesthouse in Brewster
4.98 out of 5 average rating, 105 reviewsBrand new, on a secret pond
Top guest favorite

Apartment in Brewster
5 out of 5 average rating, 26 reviewsA walk in the park
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