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Search results; Over 1,000 homes in Chester

Descriptions are based on details hosts provide
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
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 75 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
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
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
Guest favourite
Home in Chester
1844 glimmerstone Greek Revival near Okemo
5.0 out of 5 average rating, 10 reviews, 5 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
Home in Chester
Stone fireplace and deck on 4 acres
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3 bathrooms
16–21 Jul
Guest favourite
Home in Chester
Original farmhouse, 15 minutes from Okemo
4.93 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 2 bathrooms
29 Jan – 3 Feb
Top guest favourite
Cabin in Chester
Cedar tiny home with sauna and pond
4.99 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Top guest favourite
Home in Chester
1845 grist mill on the Williams River
5.0 out of 5 average rating, 104 reviews, 6 bedrooms, 9 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
15–20 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
Cabin in Grafton
Hillside log cabin with mountain views
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Home in Ludlow
Hot tub, sauna, and fire pit near Okemo
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 2 bathrooms
15–20 Jul
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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
Superhost
Place to stay in Chester
Ski club house 12 miles from Okemo
1 bedroom, 2 beds, 1 bathroom
16–21 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
15–20 Jul