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Search results; Over 1,000 homes in Chester

Top guest favourite
Room in Chester
Farm at Williams River House - Essex Suite
1 bedroom, 1 bed, 1 private bathroom
11–16 Jul
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5.0 out of 5 average rating, 44 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
31 Aug – 5 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
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
12–17 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
12–17 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
11–16 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
19–24 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
20–25 Jul
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
4.97 out of 5 average rating, 472 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.96 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
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
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
Top guest favourite
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
4.99 out of 5 average rating, 146 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Aug
Top guest favourite
Farm stay in Baltimore
Hawk Mtn Farm's lovely one bedroom apartment!
4.94 out of 5 average rating, 139 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Home in Plymouth
Charming pet-friendly retreat in the Vermont woods
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Home in Mount Holly
Cozy 2 bedroom house, close to Okemo & Killington
4.98 out of 5 average rating, 56 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Weathersfield
Cute VT Bungalow With 180 Degree View of NH
4.97 out of 5 average rating, 153 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Guest favourite
Room in Chester
Tool Shed Cabin
4.83 out of 5 average rating, 6 reviews, 1 bed, 1 bathroom
17–22 Jul