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Search results; Over 1,000 homes in Chester

Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
28 Sept – 3 Oct
4.92 out of 5 average rating, 13 reviews
Home in Middlefield
Cozy Berkshires home with brook & sugar house
3 bedrooms, 3 beds, 1 bathroom
15–20 Sept
New place to stay
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms, 3 beds, 3 bathrooms
9–14 Nov
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Becket
Forest Home with Sauna
3 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 35 reviews
Guest favourite
Cabin in Becket
Tranquil Lake cabin with Kayaks
2 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.86 out of 5 average rating, 42 reviews
Guest favourite
Home in Becket
Pristine Home In Becket Woods
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.91 out of 5 average rating, 46 reviews
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
4 bedrooms, 7 beds, 3 bathrooms
25–30 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 45 reviews
Guest favourite
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.88 out of 5 average rating, 378 reviews
Top guest favourite
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds, 4.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 24 reviews
Home in Chester
The Cottage at Quill Hollow
3 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Guest favourite
Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
4.99 out of 5 average rating, 222 reviews
Top guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
28 Sept – 3 Oct
4.91 out of 5 average rating, 126 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 Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews