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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
31 Jul – 5 Aug
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
24–29 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
12–17 Aug
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
21–26 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
22–27 Jul
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4.87 out of 5 average rating, 60 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
2–7 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
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
Flat in Londonderry
Bread and Butter Apartment
4.99 out of 5 average rating, 94 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 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
23–28 Jul
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
27 Jul – 1 Aug
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
4.97 out of 5 average rating, 472 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 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
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
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
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
26–31 Jul
Guest favourite
Home in Andover
Mountain Retreat | Hot Tub | 9 Acres | Views
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 7 beds, 2 bathrooms
28 Jul – 2 Aug