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Search results; Over 1,000 homes in Chester

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Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
3 bedrooms, 3 beds, 2 private bathrooms
16–21 Aug
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4.87 out of 5 average rating, 143 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 81 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
8–13 Aug
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 475 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
24–30 Aug
4.96 out of 5 average rating, 94 reviews
Guest favourite
Flat in Chester
Spacious, Sunny, Second Story 2 Bedroom Apartment
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 60 reviews
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 108 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Treehouse in Jamaica
The Treehouse at Frog Pond Farm
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Ludlow
The Evergreen Chal-A
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Ludlow
Ludlow Retreat-Hot Tub, Sauna & Game Room
4 bedrooms, 7 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Aug
4.87 out of 5 average rating, 62 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Ludlow
Sunny Summer Cabin | Scenic Views + Deck
3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
4.98 out of 5 average rating, 64 reviews
Guest favourite
Room in Chester
Tool Shed Cabin
1 bed, 1 bathroom
8–13 Aug
4.86 out of 5 average rating, 7 reviews