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Search results; Over 1,000 homes in Cheshire

Superhost
Home in Cheshire
Restored 1815 barn with a swimmable brook
3 bedrooms, 6 beds, 2 private baths
Aug 30 – Sep 4
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4.86 out of 5 average rating, 227 reviews
Guest favorite
Townhouse in Cheshire
Fireplace and fire pit in the Berkshires
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 1.5 baths
Aug 21 – 26
Guest favorite
Cabin in Cheshire
Deco-era cabin with a brook and fire pit
4.9 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1 bath
Sep 3 – 8
Guest suite in Cheshire
Peaceful suite near the Appalachian Trail
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bath
Aug 19 – 24
Guest favorite
Cottage in Lanesborough
Lakeside peninsula cottage with abundant wildlife
4.85 out of 5 average rating, 297 reviews, 3 bedrooms, 4 beds, 2.5 baths
Oct 5 – 10
Top guest favorite
Cottage in Hinsdale
Lake views and a fire pit
4.99 out of 5 average rating, 167 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 23 – 28
Guest favorite
Home in Cheshire
Waterfront with private lake access and kayak
4.86 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 31 – Sep 5
Guest favorite
Home in Pittsfield
Grand piano and a game room
4.96 out of 5 average rating, 228 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
Top guest favorite
Cabin in Florida
30 acres with Mt. Greylock views
4.99 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 18 – 23
Guest favorite
Guest suite in Lanesborough
Fireplace and one road to slopes
4.8 out of 5 average rating, 96 reviews, 1 bedroom, 2 beds, 1 bath
Aug 16 – 21
Guest favorite
Cabin in Hinsdale
Lakehouse with a wood stove and kayaks
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
Top guest favorite
Guesthouse in Lanesborough
1820 carriage house near Mount Greylock
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 26 – 31
Guest favorite
Apartment in Pittsfield
Newly renovated, minutes from ski and downtown
4.92 out of 5 average rating, 324 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Superhost
Apartment in Adams
Penthouse with 12-ft ceilings near MASS MoCA
4.77 out of 5 average rating, 39 reviews, 1 bedroom, 3 beds, 1.5 baths
Aug 23 – 28
Top guest favorite
Home in Pittsfield
Colonial home with a porch and yard
4.97 out of 5 average rating, 71 reviews, 3 bedrooms, 3 beds, 1.5 baths
Aug 23 – 28
Guest favorite
Home in Petersburgh
Rustic A-frame with 300 acres of trails
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bath
Aug 23 – 28
Guest favorite
Cottage in Lanesborough
Lakefront with a dock and fire pit
4.73 out of 5 average rating, 11 reviews, 2 bedrooms, 6 beds, 1 bath
Sep 14 – 19
Guest favorite
Home in Williamstown
Floor-to-ceiling Berkshire views and a hot tub
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 5 beds, 2.5 baths
Aug 20 – 25
Top guest favorite
Home in Savoy
Log cabin against the State Forest
4.94 out of 5 average rating, 88 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 16 – 21