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
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Jul 18 – 25
$116 per night
Guest favorite
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Nov 28 – Dec 5
$125 per night
Guest favorite
Apartment in Stamford
4.86 out of 5 average rating, 274 reviewsGetaway Near Mass MoCA, Great Hiking, Scenic Views
Feb 4 – 11
$99 per night
Superhost
Home in Dalton
4.92 out of 5 average rating, 170 reviewsBrooksong, the perfect Berkshires getaway
Jan 24 – 31
$329 per night
Guest favorite
Home in Cheshire
4.8 out of 5 average rating, 144 reviewsLarge Secluded Berkshire Home
Aug 19 – 26
$338 per night
Guest favorite
Home in Cheshire
5.0 out of 5 average rating, 21 reviewsThe Berkshires Hummingbird House
Oct 17 – 24
$185 per night
Guest favorite
Apartment in Adams
4.88 out of 5 average rating, 57 reviewsMountain Living, 1-bedroom unit, outdoor hot-tub
Sep 5 – 12
$86 per night
Guest favorite
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Nov 30 – Dec 7
$112 per night
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