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Search results; Over 1,000 homes in Cheshire

Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
4–9 Sept
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4.89 out of 5 average rating, 177 reviews
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 135 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
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
Townhouse in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 4 beds, 1.5 bathrooms
6–11 Sept
4.7 out of 5 average rating, 10 reviews
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
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.87 out of 5 average rating, 31 reviews
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
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
3 bedrooms, 4 beds, 2.5 bathrooms
31 Oct – 5 Nov
4.85 out of 5 average rating, 300 reviews
Guest favourite
Home in Lanesborough
Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
6 bedrooms, 10 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Lanesborough
Berkshires Home-Near Williams College
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 30 reviews
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
Top 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, 149 reviews
Guest favourite
Guest suite in Cheshire
Respite in the 'Shire
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
3–8 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Guest house in Lanesborough
The Carriage House: Spotless, Charming 2 Bedroom
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 20 reviews
Guest favourite
Room in Cheshire
#1 Large room and bathroom in beautiful old house
1 queen bed, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 7 reviews
Superhost
Townhouse in Lanesborough
Luxurious Historic Farmhouse
5 bedrooms, 10 beds, 2.5 bathrooms
4–9 Sept
4.88 out of 5 average rating, 8 reviews