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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
16–21 Aug
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4.96 out of 5 average rating, 181 reviews
Guest favourite
Room in Chester
Tool Shed Cabin
1 bed, 1 bathroom
1–6 Aug
4.86 out of 5 average rating, 7 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.86 out of 5 average rating, 79 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 78 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
New place to stay
Superhost
Room in Chester
Milk House Cabin
1 bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Room in Chester
Farm at Williams River House - Essex Suite
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Room in Rockingham
Old Victorian Charms and comfort
1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.93 out of 5 average rating, 169 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 164 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 91 reviews
Superhost
Room in Chester
Ski Club House - Ensuite Twin Bedroom - w 3/4 Bath
2 single beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Aug
4.87 out of 5 average rating, 61 reviews
Superhost
Home in Ludlow
Downtown | Hot Tub, Speakeasy, GameRoom, Fireplace
6 bedrooms, 7 beds, 2.5 bathrooms
1–6 Aug
New place to stay
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 23 reviews