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Search results; Over 1,000 homes in Chester

Guest favourite
Home in Chester
Remington Ridge
5 bedrooms, 5 beds, 2.5 private bathrooms
22–27 Sept
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5.0 out of 5 average rating, 11 reviews
Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
12–17 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
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Sept
4.87 out of 5 average rating, 62 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.87 out of 5 average rating, 83 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, 85 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
13–18 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
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 100 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 4 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
Guest favourite
Home in Chester
Modern Cabin | Near Okemo & Chester
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
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
12–17 Sept
4.93 out of 5 average rating, 165 reviews
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 11 reviews
Tiny home in Ludlow
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
New place to stay
Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 28 reviews