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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
6–11 Sept
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4.89 out of 5 average rating, 124 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 83 reviews
Guest favourite
Hotel in Chester
Quaint Queen Room & Private Bath
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 52 reviews
Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
5–10 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, 2.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
16–21 Nov
4.98 out of 5 average rating, 85 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Springfield
1794 Vermont Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Springfield
Historical Mansion Village View
6 bedrooms, 5 beds, 4.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
5–10 Sept
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
5 bedrooms, 10 beds, 2.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 154 reviews
Guest favourite
Home in Chester
Luxury, Historic home easy drive to ski areas.
6 bedrooms, 8 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 25 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Chester
Remington Ridge
5 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
7–13 Sept
4.96 out of 5 average rating, 99 reviews