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Search results; Over 1,000 homes in Chester

Superhost
Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
3 bedrooms, 3 beds, 2 private bathrooms
13–18 Sept
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4.86 out of 5 average rating, 148 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.87 out of 5 average rating, 83 reviews
Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 84 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
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Baltimore
Tarbell Farm on the hill top
2 bedrooms, 2 beds, 1 bathroom
15–20 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, 15 reviews
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
5 bedrooms, 10 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 154 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
14–20 Sept
4.96 out of 5 average rating, 100 reviews
Top guest favourite
Cabin in Ludlow
Sunny Summer Cabin | Scenic Views + Deck
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Farm stay in Baltimore
Hawk Mtn Farm's lovely one bedroom apartment!
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.94 out of 5 average rating, 142 reviews
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
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
Loft in Rockingham
Saxtons River Studio apartment
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 107 reviews
Guest favourite
Home in Grafton
Pettengill Schoolhaus scenic 2 min to main village
Individual host
13–18 Sept
4.83 out of 5 average rating, 24 reviews