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Search results; Over 1,000 homes in Cheshire

Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 private bathrooms
30 Aug – 4 Sept
,
4.86 out of 5 average rating, 226 reviews
Townhouse in Cheshire
4 Bedrooms first floor home.
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4.96 out of 5 average rating, 56 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
Guest favourite
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
4.81 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
4.9 out of 5 average rating, 174 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
Guest favourite
Room in Cheshire
#1 Large room and bathroom in beautiful old house
5.0 out of 5 average rating, 6 reviews, 1 queen bed, 1 bathroom
1–6 Sept
Top guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
4.99 out of 5 average rating, 166 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Charlemont
Stone Ridge Cottage
5.0 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
4.85 out of 5 average rating, 296 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
Superhost
Flat in Adams
Park Street Penthouse
4.78 out of 5 average rating, 37 reviews, 1 bedroom, 3 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Cabin in New Ashford
Rustic Cabin with Wood Fireplace
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
4.79 out of 5 average rating, 19 reviews, 1 bed, 2 bathrooms
22–27 Jul
Home in Worthington
Private Berkshire Chalet in Worthington
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Superhost
Apartment in Adams
Downtown Adams Vintage Getaway
4.75 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Barn in Florida
The Red Barn- close to ski mountains & museums
4.96 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
4.88 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
4.84 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Guest suite in Cheshire
Respite in the 'Shire
New place to stay, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Guest favourite
Home in Lanesborough
Berkshires Home-Near Williams College
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul