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Search results; Over 1,000 homes in Chester

Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
28 Sept – 3 Oct
4.88 out of 5 average rating, 8 reviews
Guest favourite
Cabin in Becket
Berkshires! Walk to LAKE, kayaks, dog friendly.
1 bedroom, 5 beds, 1 bathroom
25–30 Aug
4.92 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms, 3 beds, 3 bathrooms
22–27 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Becket
Forest Home with Sauna
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Otis
Enjoy every season the Berkshires have to offer.
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 129 reviews
Top guest favourite
Cabin in Becket
Entire Private Log Cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 63 reviews
Top guest favourite
Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 Aug
4.98 out of 5 average rating, 264 reviews
Guest favourite
Cabin in Becket
Cozy Cottage in the Woods
2 bedrooms, 4 double beds, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 39 reviews
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
23–28 Oct
4.99 out of 5 average rating, 167 reviews
Guest favourite
Room in Becket
Farmhouse Suite on Berkshire Farm
1 double bed, 1 bathroom
21–26 Aug
4.93 out of 5 average rating, 160 reviews
Top guest favourite
Flat in Northampton
Cozy Haven: Convenience & Charm
1 bedroom, 2 queen beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 263 reviews
Top guest favourite
Room in Northampton
Warm Country Home Minutes from Town
1 queen bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 911 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 214 reviews
Guest favourite
Cabin in Otis
Berkshires Cedar Cabin: complete privacy
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 10 reviews