Vacation rentals in Cheshire
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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
Get the amount of space that is right for you
Popular amenities for Cheshire vacation rentals
Other great vacation rentals in Cheshire
Guest favorite
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Feb 7 – 14
G$32,430 GYD per night
Guest favorite
Guesthouse in Stephentown
5.0 out of 5 average rating, 360 reviewsDog Friendly Studio
Nov 24 – Dec 1
G$39,845 GYD per night
Guest favorite
Home in Dalton
4.92 out of 5 average rating, 170 reviewsBrooksong, the perfect Berkshires getaway
Jan 30 – Feb 6
G$79,016 GYD per night
Guest favorite
Apartment in Bennington
4.93 out of 5 average rating, 527 reviewsThe Octopus's Garden
Jul 30 – Aug 6
G$20,315 GYD per night
Guest favorite
Apartment in North Adams
4.91 out of 5 average rating, 112 reviewsCozy 1 bedroom 1/2 mile to MassMoca
Aug 26 – Sep 2
G$21,263 GYD per night
Guest favorite
Home in Cheshire
5.0 out of 5 average rating, 22 reviewsThe Berkshires Hummingbird House
Mar 30 – Apr 6
G$44,372 GYD per night
Superhost
Apartment in Adams
4.91 out of 5 average rating, 22 reviewsDowntown Studio in Adams
Dec 30 – Jan 6
G$21,258 GYD per night
Guest favorite
Apartment in Adams
4.88 out of 5 average rating, 57 reviewsMountain Living, 1-bedroom unit, outdoor hot-tub
Sep 4 – 11
G$20,739 GYD per night
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