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Search results; Over 1,000 homes in Chester

Guest favourite
Tiny home in Chester
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo
1 bedroom, 1 bed, 1 private bathroom
28 Aug – 2 Sept
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4.96 out of 5 average rating, 183 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 82 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
4–9 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 97 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.87 out of 5 average rating, 82 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.87 out of 5 average rating, 62 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
24–29 Aug
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
4.93 out of 5 average rating, 165 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Superhost
Cabin in Peru
Hapgood Hollow | Modern Cabin | Sauna | Skiing
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Chester
Remington Ridge
5 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 11 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, 43 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 107 reviews
Guest favourite
Home in Grafton
Pettengill Schoolhaus scenic 2 min to main village
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Sept
4.83 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4 bedrooms, 6 beds, 1.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 77 reviews