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Search results; Over 1,000 homes in Chester

Guest favourite
Cottage in Chester
Quaint stone house!
3 bedrooms, 3 beds, 1.5 private bathrooms
13–18 Sept
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4.89 out of 5 average rating, 124 reviews
Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds
7–12 Sept
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
7–12 Sept
4.87 out of 5 average rating, 62 reviews
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds
9–14 Sept
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds
7–12 Sept
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds
9–14 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds
9–14 Sept
4.87 out of 5 average rating, 83 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed
16–21 Nov
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds
8–13 Sept
4.96 out of 5 average rating, 99 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
Modern Cabin | Near Okemo & Chester
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Hotel in Chester
Quaint Queen Room & Private Bath
1 bedroom, 1 queen bed
25–30 Oct
4.92 out of 5 average rating, 52 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds
8–13 Sept
4.85 out of 5 average rating, 46 reviews
Guest favourite
Flat in Chester
Spacious, Sunny, Second Story 2 Bedroom Apartment
2 bedrooms, 2 beds
1–6 Oct
4.9 out of 5 average rating, 60 reviews
Guest favourite
Home in Chester
Remington Ridge
5 bedrooms, 5 beds
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed
9–14 Sept
4.99 out of 5 average rating, 83 reviews
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds
8–13 Sept
5.0 out of 5 average rating, 10 reviews