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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
2–7 Aug
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4.87 out of 5 average rating, 142 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 78 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
New place to stay
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 11 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
4.85 out of 5 average rating, 46 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.86 out of 5 average rating, 80 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 82 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
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 474 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 93 reviews
Guest favourite
Home in Weston
4 Bedroom Family Ski House w/ WiFi, cable!
4 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
4.87 out of 5 average rating, 120 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, 83 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
3–8 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
3 bedrooms, 6 beds, 1.5 bathrooms
3–8 Aug
4.95 out of 5 average rating, 320 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
Home in Ludlow
Ludlow Retreat-Hot Tub, Sauna & Game Room
4 bedrooms, 7 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Mount Holly
Cozy 2 bedroom house, close to Okemo & Killington
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 59 reviews