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Search results; Over 1,000 homes in Chester

Guest favourite
Home in Chester
Vermont 1828 Reunion House, near Okemo
8 bedrooms, 11 beds, 4 private bathrooms
5–10 Aug
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4.8 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed
13–18 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
9–14 Aug
5.0 out of 5 average rating, 12 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds
15–20 Aug
New place to stay
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds
6–11 Aug
4.85 out of 5 average rating, 46 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds
15–20 Aug
4.86 out of 5 average rating, 81 reviews
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed
18–23 Aug
4.99 out of 5 average rating, 82 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds
5–10 Aug
4.87 out of 5 average rating, 61 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds
20–25 Aug
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Flat in Andover
Private Hilltop farm apartment
1 bedroom, 1 double bed
23–28 Aug
4.97 out of 5 average rating, 475 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed
6–11 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Cabin in Grafton
Log cabin getaway
1 bedroom, 2 beds
9–14 Aug
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds
10–15 Aug
4.93 out of 5 average rating, 164 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds
8–13 Sept
Guest favourite
Home in Weston
4 Bedroom Family Ski House w/ WiFi, cable!
4 bedrooms, 5 beds
15–20 Aug
4.87 out of 5 average rating, 120 reviews
Guest favourite
Room in Chester
Tool Shed Cabin
1 bed
5–10 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Cabin in Ludlow
Sunny Summer Cabin | Scenic Views + Deck
3 bedrooms, 5 beds
18–23 Aug
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds
24–29 Aug
5.0 out of 5 average rating, 104 reviews