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Search results; Over 1,000 homes in Cheshire

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Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 private bathrooms
21–26 Jun
,
4.86 out of 5 average rating, 226 reviews
Flat in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 6 beds, 1.5 bathrooms
20–25 Jun
Place to stay in Cheshire
#1 Large room and bathroom in beautiful old house
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
7–12 Jul
4.9 out of 5 average rating, 172 reviews
Top guest favourite
Home in Savoy
Bear Minimum
2 bedrooms, 2 queen beds, 2.5 bathrooms
21–26 Jun
4.94 out of 5 average rating, 84 reviews
Top guest favourite
Home in Pownal
Cozy Home in Pownal VT
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 164 reviews
Top guest favourite
Cabin in Pownal
La Finca - Cozy A-Frame with Lofts & Views
2 bedrooms, 4 beds, 1 bathroom
29 Jun – 4 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 201 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
21–26 Jun
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 307 reviews
Guest favourite
Flat in Williamstown
COLD SPRING
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Jun
4.94 out of 5 average rating, 352 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
12–17 Jul
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 132 reviews
Top guest favourite
Flat in North Adams
Berkshire Mountain Top Chalet
3 bedrooms, 4 beds, 2 bathrooms
20–25 Jun
4.94 out of 5 average rating, 182 reviews
Top guest favourite
Flat in North Adams
Charming Art Filled Apartment
3 bedrooms, 3 queen beds, 1 bathroom
28 Jun – 3 Jul
4.97 out of 5 average rating, 178 reviews
Top guest favourite
Home in Williamstown
Elegant Mountain View Retreat By Evergreen Home
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Jun
4.99 out of 5 average rating, 67 reviews