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Search results; Over 1,000 homes in Chester

Top guest favourite
Room in Chester
Farm at Williams River House - Gloucester Suite
1 bedroom, 1 bed, 1.5 private bathrooms
13–18 Jul
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5.0 out of 5 average rating, 24 reviews
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
12–17 Jul
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
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5.0 out of 5 average rating, 10 reviews, 5 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
20–25 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
11–16 Jul
Top guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
5.0 out of 5 average rating, 104 reviews, 6 bedrooms, 9 beds, 3 bathrooms
14–19 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
10–15 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
10–15 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
Home in Chester
Quaint Farmhouse
4.93 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 2 bathrooms
29 Jan – 3 Feb
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
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
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
9–14 Jul
Superhost
Place to stay in Chester
Ski Club House - Ensuite Twin Bedroom - w 3/4 Bath
1 bedroom, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
4.99 out of 5 average rating, 150 reviews, 5 bedrooms, 10 beds, 2.5 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Andover
Mountain Retreat | Hot Tub | 9 Acres | Views
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 7 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Cabin in Grafton
Log cabin getaway
4.94 out of 5 average rating, 16 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul