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Search results; Over 1,000 homes in Chester

Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
18–23 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.93 out of 5 average rating, 164 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, 77 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 32 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Springfield
1794 Vermont Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Home in Mount Holly
Cozy 2 bedroom house, close to Okemo & Killington
2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Room in Rockingham
Charming old Victorian home
1 queen bed, 1 bathroom
24–29 Jul
4.95 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Grafton
Log cabin getaway
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed, 1 bathroom
20–25 Jul
4.97 out of 5 average rating, 472 reviews
Top guest favourite
Home in Ludlow
Private Mountain House with hot tub and A/C
3 bedrooms, 6 beds, 3 bathrooms
18–23 Jul
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.96 out of 5 average rating, 101 reviews
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
2 bedrooms, 3 beds, 1 bathroom
5–10 Aug
4.99 out of 5 average rating, 146 reviews