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Search results; Over 1,000 homes in Chester

Superhost
Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
3 bedrooms, 3 beds, 2 private bathrooms
14–19 Sept
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4.86 out of 5 average rating, 148 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 83 reviews
Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
16–21 Nov
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.87 out of 5 average rating, 62 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
14–20 Sept
4.96 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 84 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.85 out of 5 average rating, 46 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
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Cabin in Ludlow
Classic Vermont Cabin | Scenic Views + Deck
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 28 reviews
Tiny home in Ludlow
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
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