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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, 76 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, 11 reviews, 3 bedrooms, 6 beds, 3 bathrooms
19–24 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
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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
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
20–25 Jul
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
4.86 out of 5 average rating, 78 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Home in Chester
Okemo Valley Chalet
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 13 beds, 2.5 bathrooms
24–29 Jul
Barn in Chester
1850's converted barn apartment in Chester
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
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
Cabin in Ludlow
Sunny Summer Cabin | Scenic Views + Deck
4.98 out of 5 average rating, 64 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
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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
21–26 Jul
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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
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Home in Ludlow
Private Mountain House with hot tub and A/C
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Apartment in Ludlow
Lovely 1-Bedroom condo with indoor fireplace!
4.95 out of 5 average rating, 191 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
4.96 out of 5 average rating, 101 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
4.99 out of 5 average rating, 150 reviews, 5 bedrooms, 10 beds, 2.5 bathrooms
30 Jul – 4 Aug
Guest favourite
Room in Chester
Tool Shed Cabin
4.86 out of 5 average rating, 7 reviews, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
4.99 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Aug