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Search results; Over 1,000 homes in Chester

Top guest favorite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 bed, 1 private bath
Sep 13 – 18
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4.98 out of 5 average rating, 81 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds
Aug 15 – 20
Guest favorite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds
Aug 17 – 22
4.86 out of 5 average rating, 81 reviews
Top guest favorite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed
Aug 28 – Sep 2
4.99 out of 5 average rating, 82 reviews
Top guest favorite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds
Aug 19 – 24
5.0 out of 5 average rating, 12 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds
Aug 13 – 18
4.85 out of 5 average rating, 46 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds
Aug 23 – 28
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed
Aug 13 – 18
4.97 out of 5 average rating, 38 reviews
Top guest favorite
Apartment in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds
Aug 13 – 18
4.93 out of 5 average rating, 165 reviews
Top guest favorite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds
Aug 24 – 30
4.96 out of 5 average rating, 95 reviews
Guest favorite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds
Sep 7 – 12
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds
Aug 24 – 29
5.0 out of 5 average rating, 105 reviews
Top guest favorite
Cabin in Grafton
Log cabin getaway
1 bedroom, 2 beds
Aug 16 – 21
4.95 out of 5 average rating, 22 reviews
Top guest favorite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds
Aug 27 – Sep 1
5.0 out of 5 average rating, 32 reviews
Top guest favorite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed
Sep 7 – 12
4.96 out of 5 average rating, 108 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds
Sep 8 – 13
Guest favorite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds
Aug 28 – Sep 2
4.87 out of 5 average rating, 62 reviews
Guest favorite
Home in Chester
Remington Ridge
5 bedrooms, 5 beds
Aug 24 – 29
5.0 out of 5 average rating, 11 reviews
Top guest favorite
Home in West Windsor
Chuck's Place
3 bedrooms, 6 beds
Aug 30 – Sep 4
4.96 out of 5 average rating, 92 reviews