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Search results; Over 1,000 homes in Chester

Guest favourite
Tiny home in Chester
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo
1 bedroom, 1 bed, 1 private bathroom
27 Aug – 1 Sept
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4.96 out of 5 average rating, 183 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
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
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
20–25 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
18–23 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
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Room in Rockingham
Eva Blake House-Margaret's Room
1 double bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 138 reviews
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Springfield
1794 Vermont Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Guest house in Rockingham
Peaceful Historic Cottage
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 73 reviews
Top guest favourite
Cabin in Townshend
Goldfinch Hollow: Tucked Within 5 Private Acres
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 84 reviews
Guest favourite
Home in Grafton
Pettengill Schoolhaus scenic 2 min to main village
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Sept
4.83 out of 5 average rating, 24 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, 475 reviews
Top guest favourite
Tiny home in Brookline
Majestic Vermont Tiny Home/Guest House
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 7 reviews