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Search results; Over 1,000 homes in Chester

Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bedroom, 1 bed, 1 private bathroom
7–12 Jul
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5.0 out of 5 average rating, 27 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 75 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 3 bathrooms
7–12 Jul
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
4.99 out of 5 average rating, 80 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
4.86 out of 5 average rating, 77 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
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
7–12 Jul
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
4.96 out of 5 average rating, 97 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
4.97 out of 5 average rating, 471 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
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
8–13 Jul
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jul
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
26–31 Jul
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Room in Rockingham
Charming old Victorian home
4.95 out of 5 average rating, 59 reviews, 1 queen bed, 1 bathroom
17–22 Jul
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.95 out of 5 average rating, 88 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Guest favourite
Room in Chester
Tool Shed Cabin
4.83 out of 5 average rating, 6 reviews, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Apartment in Ludlow
Lovely 1-Bedroom condo with indoor fireplace!
4.95 out of 5 average rating, 190 reviews, 1 bedroom, 3 beds, 1 bathroom
7–12 Jul
Top guest favourite
Barn in Rockingham
Quiet Country Retreat
5.0 out of 5 average rating, 40 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul