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Search results; Over 1,000 homes in Chester

Superhost
Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
3 bedrooms, 3 beds, 2 private bathrooms
29 Aug – 3 Sept
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4.86 out of 5 average rating, 144 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.86 out of 5 average rating, 81 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 81 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
19–24 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Room in Chester
Tool Shed Cabin
1 bed, 1 bathroom
19–24 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Shared room in Cavendish
YakPod #3 Snowed Inn Pod Lodge :12 min from Okemo!
1 bedroom, 1 bed, 1 shared bathroom
19–24 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
24–30 Aug
4.96 out of 5 average rating, 95 reviews
Top guest favourite
Room in Rockingham
Eva Blake House-Margaret's Room
1 double bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 138 reviews
Top guest favourite
Home in South Londonderry
Cozy barn apartment in So. Vermont
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 335 reviews
Top guest favourite
Farm stay in Baltimore
Hawk Mtn Farm's lovely one bedroom apartment!
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 477 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.97 out of 5 average rating, 38 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.87 out of 5 average rating, 62 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 106 reviews
Top guest favourite
Room in Danby
Spectacular view, private bathroom. One king bed
1 king bed, 1.5 bathrooms
23–28 Aug
4.99 out of 5 average rating, 237 reviews
Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 28 reviews