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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 queen bed
31 Aug – 5 Sept
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds
31 Jul – 5 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed
24–29 Jul
4.99 out of 5 average rating, 81 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds
12–17 Aug
4.86 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds
21–26 Jul
4.93 out of 5 average rating, 164 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds
22–27 Jul
4.85 out of 5 average rating, 46 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds
2–7 Aug
4.87 out of 5 average rating, 60 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed
26–31 Jul
4.97 out of 5 average rating, 38 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds
15–20 Aug
New place to stay
Top guest favourite
Flat in Londonderry
Bread and Butter Apartment
2 bedrooms, 2 beds
2–7 Aug
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds
23–28 Jul
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4 bedrooms, 6 beds
27 Jul – 1 Aug
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed
21–26 Jul
4.97 out of 5 average rating, 472 reviews
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed
18–23 Aug
4.96 out of 5 average rating, 101 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds
24–29 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
5 bedrooms, 10 beds
30 Jul – 4 Aug
4.99 out of 5 average rating, 150 reviews
Top guest favourite
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
2 bedrooms, 3 beds
26–31 Jul
4.99 out of 5 average rating, 147 reviews
Guest favourite
Home in Andover
Mountain Retreat | Hot Tub | 9 Acres | Views
4 bedrooms, 7 beds
28 Jul – 2 Aug
5.0 out of 5 average rating, 29 reviews