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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
12–17 Jul
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4.86 out of 5 average rating, 226 reviews
Flat in Cheshire
4 Bedrooms first floor home.
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
4–9 Jul
Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4.96 out of 5 average rating, 55 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
4.81 out of 5 average rating, 160 reviews, 3 bedrooms, 5 beds, 2 bathrooms
5–10 Jul
Guest favourite
Home in Cheshire
6BR Renewed Historic Berkshire Gem • Hot Tub, Pool
5.0 out of 5 average rating, 9 reviews, 6 bedrooms, 8 beds, 3 bathrooms
31 Aug – 5 Sept
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
4.9 out of 5 average rating, 173 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Guest favourite
Place to stay in Cheshire
#1 Large room and bathroom in beautiful old house
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Top guest favourite
Home in Cheshire
Berkshire's Family Gathering & Mountain Escape!
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
4.88 out of 5 average rating, 24 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
4.9 out of 5 average rating, 146 reviews, 5 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
4.82 out of 5 average rating, 22 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Adams
Mount Greylock View Retreat,3 bedroom,2 1/2 bath.
4.94 out of 5 average rating, 79 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 215 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
4.99 out of 5 average rating, 132 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
Top guest favourite
Home in Lanesborough
The Pond House
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
Guest favourite
Room in Adams
Summer Green 3 Adult Size Twin Beds Pvt Bthrm
4.89 out of 5 average rating, 27 reviews, 3 single beds, No bathroom
2–7 Jul
Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
4.96 out of 5 average rating, 54 reviews, 6 bedrooms, 14 beds, 5.5 bathrooms
5–10 Jul
Superhost
Place to stay in Adams
Berkshires Summer Green
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 1 bed, 2.5 bathrooms
3–8 Jul
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
4.82 out of 5 average rating, 207 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Jul