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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, 35 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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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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Home in Becket
Forest Home with Sauna
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Sept
4.94 out of 5 average rating, 34 reviews
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Home in Becket
Fall Foliage Lakefront Retreat - Berkshires
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 45 reviews
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Guest house in Becket
Country Cabin
1 bedroom, 2 queen beds, 1 bathroom
9–14 Sept
4.92 out of 5 average rating, 292 reviews
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Cabin in Becket
Tranquil Lake cabin with Kayaks
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
4.85 out of 5 average rating, 41 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, 163 reviews
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Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.98 out of 5 average rating, 46 reviews
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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
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Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
4.81 out of 5 average rating, 81 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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Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms, 10 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 24 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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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
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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
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Home in Becket
Beautiful, quiet and cozy home in Becket!
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 154 reviews
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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