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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
18–23 Oct
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4.85 out of 5 average rating, 229 reviews
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Townhouse in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 4 beds, 1.5 bathrooms
13–18 Oct
4.7 out of 5 average rating, 10 reviews
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Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.81 out of 5 average rating, 167 reviews
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Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 60 reviews
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Top guest favourite
Guest suite in Cheshire
Respite in the 'Shire
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.91 out of 5 average rating, 149 reviews
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Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
4.89 out of 5 average rating, 177 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
3–8 Nov
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Flat in Dalton
1843 House - Bright and Airy 5 Rooms (2 Bedrooms)
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.91 out of 5 average rating, 22 reviews
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Guest favourite
Home in Cheshire
6BR Renewed Historic Berkshire Gem • Hot Tub, Pool
6 bedrooms, 8 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Williamstown
Charming Berkshire Retreat-Minutes to Williamstown
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 12 reviews
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Superhost
Flat in Adams
Guestrooms on the Bike Trail
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.63 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Adams
Greylock View Cottage
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.88 out of 5 average rating, 34 reviews
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Guest favourite
Townhouse in Hancock
Beautiful Jiminy Peak Townhome Family Friendly
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.83 out of 5 average rating, 109 reviews
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Top guest favourite
Home in Hancock
Grand 6BR Home by Jiminy | Hike • Hot Tub • Games
6 bedrooms, 14 beds, 5.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
3–8 Oct
4.97 out of 5 average rating, 78 reviews
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Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Superhost
Flat in Adams
Apartment on the Bike Trail, in the heart of Adams
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
4.52 out of 5 average rating, 79 reviews