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Vacation rentals in Cheshire
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Cheshire
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 Cheshire vacation rentals
Other great vacation rentals in Cheshire
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Guest favorite
Barn in Marlboro
4.95 out of 5 average rating, 277 reviewsThe Studio With a View. Bring your dog, too!
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Guest favorite
Guesthouse in Pownal
4.84 out of 5 average rating, 501 reviewsBauhaus Guest House in So. VT.
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Guest favorite
Rental unit in Adams
4.98 out of 5 average rating, 56 reviewsCharming/Rustic Apartment with downtown views
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Guest favorite
Home in Cheshire
5 out of 5 average rating, 33 reviewsThe Berkshires Hummingbird House
![](https://a0.muscache.com/im/pictures/29ef8931-b003-490d-8a43-24aa944396cb.jpg?im_w=720)
Superhost
Rental unit in Adams
4.87 out of 5 average rating, 30 reviewsDowntown Studio in Adams
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Guest favorite
Home in Adams
4.92 out of 5 average rating, 77 reviewsMountain View Hideaway
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Guest favorite
Home in Cheshire
4.95 out of 5 average rating, 58 reviewsBerkshire County modern home + pool
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Guest favorite
Home in North Adams
5 out of 5 average rating, 8 reviewsColorful Urban Cabin Steps from Mass MoCA
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