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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 private bathroom
7–12 Sept
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5.0 out of 5 average rating, 40 reviews
Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
5–10 Oct
4.92 out of 5 average rating, 12 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, 35 reviews
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms, 3 beds, 3 bathrooms
12–17 Oct
4.98 out of 5 average rating, 59 reviews
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds, 4.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
6–11 Sept
4.98 out of 5 average rating, 266 reviews
Top guest favourite
Flat in Otis
Enjoy every season the Berkshires have to offer.
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 132 reviews
Top guest favourite
Room in Becket
Farmhouse Suite on Berkshire Farm
1 double bed, 1 bathroom
7–13 Sept
4.93 out of 5 average rating, 164 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 151 reviews
Guest favourite
Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms, 5 beds, 3 bathrooms
2–7 Sept
4.98 out of 5 average rating, 47 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 320 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Becket
Entire Private Log Cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Farm stay in Blandford
Freeland Brook Farm - magical Berkshires view
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Cabin in Becket
Cozy Lake Side Cabin
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cabin in Becket
Tranquil Lake cabin with Kayaks
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
4.86 out of 5 average rating, 42 reviews