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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
3 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 75 reviews
Guest favourite
Hotel in Chester
1780 inn with backyard trail access
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 77 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 32 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
1844 glimmerstone Greek Revival near Okemo
5 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Home in Chester
Stone fireplace and deck on 4 acres
3 bedrooms, 5 beds, 3 bathrooms
16–21 Jul
4.85 out of 5 average rating, 46 reviews
Guest favourite
Home in Chester
Original farmhouse, 15 minutes from Okemo
3 bedrooms, 3 beds, 2 bathrooms
29 Jan – 3 Feb
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Cabin in Chester
Cedar tiny home with sauna and pond
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.93 out of 5 average rating, 164 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
4.96 out of 5 average rating, 90 reviews
Top guest favourite
Cabin in Grafton
Hillside log cabin with mountain views
1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Ludlow
Hot tub, sauna, and fire pit near Okemo
4 bedrooms, 7 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 13 reviews
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
Historic 1835 stone house near Okemo
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 38 reviews
Superhost
Place to stay in Chester
Ski Club House - Ensuite Twin Bedroom - w 3/4 Bath
1 bedroom, 2 single beds, 1 bathroom
16–21 Jul
Guest favourite
Home in Andover
9 acres with mountain views and a hot tub
4 bedrooms, 7 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 29 reviews