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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
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
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
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
5–10 Sept
4.87 out of 5 average rating, 264 reviews
Top guest favourite
Home in Becket
Beautiful, quiet and cozy home in Becket!
3 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
4.94 out of 5 average rating, 154 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
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
Guest favourite
Cabin in Becket
We call it "Becket"
2 bedrooms, 5 beds, 1 bathroom
26 Sept – 1 Oct
4.8 out of 5 average rating, 59 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
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 265 reviews
Guest favourite
Cabin in Otis
Berkshires Cedar Cabin: complete privacy
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Williamsburg
The cozy clubhouse
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 184 reviews
Top guest favourite
Home in Otis
Idyllic family retreat - spacious lake home,
4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Oct
4.95 out of 5 average rating, 175 reviews
Guest favourite
Home in Becket
Little Longbow Lakefront Chalet
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 84 reviews
Guest favourite
Home in Tolland
Cabin with Hot Tub and Lake Access
2 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Becket
Lakefront Chalet | Dock, Sauna & Fireplace
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 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