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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
27 Sept – 2 Oct
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, 13 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
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
11–16 Sept
4.92 out of 5 average rating, 123 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
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
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
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
Guest favourite
Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms, 5 beds, 3 bathrooms
5–10 Sept
4.98 out of 5 average rating, 47 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, 133 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
Top guest favourite
Cabin in Becket
Cozy Cottage in the Woods
2 bedrooms, 2 double beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 43 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
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
Guest favourite
Home in Becket
Away from it all, close to everything
3 bedrooms, 3 queen beds, 2.5 bathrooms
10–15 Jan
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
3 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 250 reviews