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Search results; Over 1,000 homes in Chester

Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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5.0 out of 5 average rating, 27 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed
13–18 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds
15–20 Aug
New place to stay
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds
2–7 Aug
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed
18–23 Aug
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed
17–22 Aug
4.97 out of 5 average rating, 474 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds
1–6 Aug
4.93 out of 5 average rating, 164 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds
15–20 Aug
4.86 out of 5 average rating, 79 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed
2–7 Aug
4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds
4–9 Aug
4.87 out of 5 average rating, 61 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds
20–25 Aug
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Home in Ludlow
Ludlow Retreat-Hot Tub, Sauna & Game Room
4 bedrooms, 7 beds
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Springfield
Scandinavian Serenity Close to Okemo
2 bedrooms, 2 beds
21–26 Aug
5.0 out of 5 average rating, 54 reviews
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
3 bedrooms, 6 beds
3–8 Aug
4.95 out of 5 average rating, 320 reviews
Guest favourite
Home in Weston
4 Bedroom Family Ski House w/ WiFi, cable!
4 bedrooms, 5 beds
15–20 Aug
4.87 out of 5 average rating, 120 reviews