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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, 36 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, 25 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
27 Aug – 1 Sept
4.89 out of 5 average rating, 9 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, 51 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, 58 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, 130 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 Sept
4.98 out of 5 average rating, 265 reviews
Guest favourite
Cabin in Becket
Cozy Cottage in the Woods
2 bedrooms, 4 double beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 40 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.97 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, 64 reviews
Cabin in Otis
Overflow Cabin Retreat on Otis Reservoir
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Room in Northampton
Warm Country Home Minutes from Town
1 queen bed, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 912 reviews
Guest favourite
Home in Otis
Berkshire Lakefront Lighthouse Getaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 78 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 317 reviews
Guest favourite
Cabin in Becket
We call it "Becket"
2 bedrooms, 5 beds, 1 bathroom
19–24 Aug
4.79 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 46 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
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, 264 reviews