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Search results; Over 1,000 homes in Cheshire

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Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 private bathrooms
27 Sept – 2 Oct
,
4.86 out of 5 average rating, 228 reviews
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Townhouse in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 4 beds, 1.5 bathrooms
6–11 Sept
4.67 out of 5 average rating, 9 reviews
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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, 59 reviews
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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
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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
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Guest favourite
Room in Cheshire
#2 Large bedroom and bath in beautiful old house.
1 queen bed, 1 bathroom
30 Oct – 6 Nov
5.0 out of 5 average rating, 5 reviews
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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
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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, 86 reviews
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Top guest favourite
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, 6 reviews
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Guest favourite
Home in Cheshire
6BR Renewed Historic Berkshire Gem • Hot Tub, Pool
6 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in North Adams
Colorful Urban Cabin Steps from Mass MoCA
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 112 reviews
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Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
1–6 Sept
4.97 out of 5 average rating, 78 reviews
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Superhost
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
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Superhost
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.96 out of 5 average rating, 230 reviews
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Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.8 out of 5 average rating, 41 reviews
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Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.82 out of 5 average rating, 211 reviews
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Guest favourite
Home in Adams
Spacious Home by Mt. Greylock
4 bedrooms, 5 beds, 3 bathrooms
4–9 Sept
4.91 out of 5 average rating, 54 reviews
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Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.69 out of 5 average rating, 97 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 19 reviews