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Search results; Over 1,000 homes in Cheshire

Top guest favourite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 bedrooms, 4 beds, 2.5 private bathrooms
7–12 Sept
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4.97 out of 5 average rating, 58 reviews
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
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
Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 bathrooms
27 Sept – 2 Oct
4.86 out of 5 average rating, 228 reviews
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, 5 reviews
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
Home in Pittsfield
Cozy lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
New place to stay
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
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
Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 552 reviews
Guest favourite
Home in Adams
Spacious Home by Mt. Greylock
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.91 out of 5 average rating, 54 reviews
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
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
1–6 Sept
4.78 out of 5 average rating, 113 reviews
Guest favourite
Home in Adams
Beautiful Victorian. The heart of the Berkshires.
5 bedrooms, 6 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 148 reviews
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
Guest favourite
Cottage in Lanesborough
Stone School Cottage
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 264 reviews
Superhost
Townhouse in Lanesborough
Luxurious Historic Farmhouse
5 bedrooms, 10 beds, 2.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 55 reviews
Guest favourite
Apartment in Adams
Downtown Adams Vintage Getaway
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.76 out of 5 average rating, 67 reviews