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Search results; Over 1,000 homes in Chester

Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 75 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
4.99 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
4.93 out of 5 average rating, 164 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
4.86 out of 5 average rating, 77 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4.96 out of 5 average rating, 74 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
15–20 Jul
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Grafton
Pettengill Schoolhaus scenic 2 min to main village
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Jul
Guest favourite
Room in Chester
Tool Shed Cabin
4.86 out of 5 average rating, 7 reviews, 1 bed, 1 bathroom
17–22 Jul
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.96 out of 5 average rating, 90 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
Home in Chester
Okemo Valley Chalet
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 13 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Flat in Londonderry
Bread and Butter Apartment
4.99 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Grafton
Log cabin getaway
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Flat in Weathersfield
Cute VT Bungalow With 180 Degree View of NH
4.97 out of 5 average rating, 153 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Top guest favourite
Home in Springfield
1794 Vermont Home
5.0 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Aug
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept