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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
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 78 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
Barn in Chester
1850's converted barn apartment in Chester
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
4.86 out of 5 average rating, 79 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
4.99 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
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
1–6 Aug
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
4.97 out of 5 average rating, 474 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4.87 out of 5 average rating, 61 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Aug
Home in Chester
Okemo Valley Chalet
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 13 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.96 out of 5 average rating, 93 reviews, 2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
Top guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
4.95 out of 5 average rating, 320 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
3–8 Aug
Top guest favourite
Room in Rockingham
Charming old Victorian home
4.95 out of 5 average rating, 64 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Weston
4 Bedroom Family Ski House w/ WiFi, cable!
4.87 out of 5 average rating, 120 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Springfield
Scandinavian Serenity Close to Okemo
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Aug
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
1–6 Aug
Top guest favourite
Home in Ludlow
Ludlow Retreat-Hot Tub, Sauna & Game Room
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 7 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
4.99 out of 5 average rating, 148 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Aug