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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
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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
18–23 Sept
4.7 out of 5 average rating, 10 reviews
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Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
4.89 out of 5 average rating, 177 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, 18 reviews
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Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
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
17–22 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
4.81 out of 5 average rating, 167 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
16–21 Sept
4.93 out of 5 average rating, 88 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 Windsor
Stone cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
4.88 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
4.91 out of 5 average rating, 149 reviews
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Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 237 reviews
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Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 560 reviews
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Superhost
Flat in Adams
Guestrooms on the Bike Trail
2 bedrooms, 3 beds, 1 bathroom
17–22 Sept
4.63 out of 5 average rating, 41 reviews
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Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.88 out of 5 average rating, 34 reviews
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Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
4.82 out of 5 average rating, 214 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
16–21 Sept
4.97 out of 5 average rating, 79 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
27 Sept – 2 Oct
4.97 out of 5 average rating, 65 reviews
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Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 20 reviews