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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, 230 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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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
6BR Renewed Historic Berkshire Gem • Hot Tub, Pool
6 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 19 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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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
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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Superhost
Guest suite in Lanesborough
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.79 out of 5 average rating, 103 reviews
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Guest favourite
Home in Lanesborough
Elmwood Farmhouse
4 bedrooms, 7 beds, 2.5 bathrooms
20–25 Oct
4.9 out of 5 average rating, 124 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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Superhost
Home in Pittsfield
The Sunset Fern Cliff House
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
New place to stay
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Guest favourite
Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 44 reviews
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Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.89 out of 5 average rating, 35 reviews
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Guest favourite
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.71 out of 5 average rating, 102 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 Oct
4.97 out of 5 average rating, 79 reviews
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Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 bathrooms
26–31 Oct
4.93 out of 5 average rating, 212 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
Home in Cheshire
Berkshire's Family Gathering & Mountain Escape!
4 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.93 out of 5 average rating, 15 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