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Search results; Over 1,000 homes in Chester

Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 private bathroom
15–20 Jul
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4.93 out of 5 average rating, 164 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
15–20 Jul
Home in Chester
Okemo Valley Chalet
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 13 beds, 2.5 bathrooms
20–25 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
15–20 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
31 Aug – 5 Sept
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
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
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
16–21 Aug
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
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
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
20–25 Jul
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4.96 out of 5 average rating, 74 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
15–20 Jul
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Ludlow
Ludlow Retreat-Hot Tub, Sauna & Game Room
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 2 bathrooms
14–19 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
Superhost
Place to stay in Chester
Ski Club House - Ensuite Twin Bedroom - w 3/4 Bath
1 bedroom, 2 beds, 1 bathroom
15–20 Jul
Top guest favourite
Home in Cavendish
VT Retreat: Hot tub | pool table | 70” TV | bbq
4.96 out of 5 average rating, 124 reviews, 4 bedrooms, 10 beds, 3 bathrooms
21–26 Jul
Guest favourite
Home in Ludlow
Updated 6BR Home 4 min to Okemo w fenced in yard!
4.93 out of 5 average rating, 97 reviews, 6 bedrooms, 10 beds, 3.5 bathrooms
19–24 Jul
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.96 out of 5 average rating, 90 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug