Search results; Over 1,000 homes in Cheshire

Superhost
Home in Cheshire
19th c. Barn in The Berkshires
3 bedrooms, 6 beds, 2 private bathrooms
21–26 Jun
,
4.86 out of 5 average rating, 226 reviews
Place to stay in Cheshire
#1 Large room and bathroom in beautiful old house
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Flat in Cheshire
4 Bedrooms first floor home.
4 bedrooms, 6 beds, 1.5 bathrooms
18–23 Jun
Guest favourite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bedroom, 1 bed, 1 bathroom
19–24 Jun
4.9 out of 5 average rating, 172 reviews
Place to stay in Cheshire
#2 Large bedroom and bath in beautiful old house.
1 bedroom, 1 bed, 1 bathroom
28 Aug – 4 Sept
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds, 2 bathrooms
6–11 Jul
4.73 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Williamstown
Berkshire Guest Suite
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 258 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
21–26 Jun
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, Toilet with sink
26–31 Jul
4.98 out of 5 average rating, 255 reviews
Top guest favourite
Home in North Adams
Bernie's & Betty's
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Jul
4.97 out of 5 average rating, 186 reviews
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 132 reviews
Guest favourite
Home in North Adams
Colorful Urban Cabin Steps from Mass MoCA
2 bedrooms, 2 beds, 1 bathroom
4–9 Aug
4.89 out of 5 average rating, 107 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.92 out of 5 average rating, 310 reviews
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Flat in Williamstown
Downtown | Waterfront | Walk to Shops
1 bedroom, 2 beds, 1 bathroom
21–26 Jun
5.0 out of 5 average rating, 162 reviews
Top guest favourite
Home in Williamstown
100 yards to Williams College.
3 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Savoy
The Camp - hiking trails right outside your door
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 247 reviews