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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
3–8 Oct
,
4.86 out of 5 average rating, 227 reviews
Townhouse in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 4 beds, 1.5 bathrooms
6–11 Sept
4.63 out of 5 average rating, 8 reviews
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
3–8 Sept
4.89 out of 5 average rating, 176 reviews
Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 58 reviews
Guest favourite
Guest suite in Cheshire
Respite in the 'Shire
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 134 reviews
Home in Adams
Relaxing Berkshires Home With a View!
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.87 out of 5 average rating, 30 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Home in Adams
Mount Greylock View Retreat,3 bedroom,2 1/2 bath.
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 84 reviews
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.81 out of 5 average rating, 210 reviews
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.81 out of 5 average rating, 165 reviews
Guest favourite
Cottage in Lanesborough
Stone School Cottage
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 263 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 83 reviews
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.87 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Lanesborough
The Carriage House: Spotless, Charming 2 Bedroom
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Barn in Florida
The Red Barn- close to ski mountains & museums
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Flat in North Adams
The MoCA-Cabana: 2 bd + Sauna
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 143 reviews
Top guest favourite
Cabin in Plainfield
Peaceful Lakeside Cabin
1 bed, 1 bathroom
20–25 Jun
4.96 out of 5 average rating, 26 reviews