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Search results; Over 1,000 homes in Chester

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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, 39 reviews
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Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 36 reviews
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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
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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
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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
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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
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Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 131 reviews
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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
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Cabin in Cummington
Just Be Cabin
1 double bed, WC
1–6 Sept
4.98 out of 5 average rating, 266 reviews
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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, 59 reviews
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Flat in Williamsburg
The cozy clubhouse
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 183 reviews
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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
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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
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Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 49 reviews
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Flat in Northampton
Light filled three bedroom apartment DT Florence!
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 490 reviews
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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
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Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 11 reviews
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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
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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