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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 bed, 1 private bathroom
8–13 Aug
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4.97 out of 5 average rating, 74 reviews
Guest favourite
Home in Chester
4BR-4BA/Fireplace/Near Skiing/Walk to Shops
4 bedrooms, 8 single beds, 4 bathrooms
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
5.0 out of 5 average rating, 9 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
9–14 Jul
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
New place to stay
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 Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 32 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
18–23 Jul
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
3–8 Jul
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, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
2 bedrooms, 2 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 23 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
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
3–8 Jul
4.93 out of 5 average rating, 164 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, 317 reviews
Guest favourite
Home in Andover
River House w/ Hot Tub! Close to Mountain & More
4 bedrooms, 7 beds, 2.5 bathrooms
2–7 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Ludlow
Updated 6BR Home 4 min to Okemo w fenced in yard!
6 bedrooms, 10 beds, 3.5 bathrooms
19–24 Jul
4.93 out of 5 average rating, 95 reviews
Home in Londonderry
Timberframe Private Retreat in Green Mountains
2 bedrooms, 4 beds, 2 bathrooms
2–7 Jul
Top guest favourite
Home in Grafton
Pettengill Schoolhaus scenic 2 min to main village
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Jul
4.94 out of 5 average rating, 18 reviews