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Search results; Over 1,000 homes in Chester

Home in Chester
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
2 bedrooms, 2 beds, 1 bathroom
30 Jun – 5 Jul
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4.76 out of 5 average rating, 29 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
20–25 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
Superhost
Room in Chester
Ski Club House - Ensuite Twin Bedroom - w 3/4 Bath
2 single beds, 1 bathroom
15–20 Sept
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
16–21 Sept
5.0 out of 5 average rating, 3 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, 86 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 6 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 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
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.96 out of 5 average rating, 100 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 Springfield
1794 Vermont Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 85 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
Superhost
Room in Chester
Milk House Cabin
1 bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
Luxury, Historic home easy drive to ski areas.
6 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 25 reviews
Superhost
Room in Chester
Tool Shed Cabin
1 bed, 1 bathroom
14–19 Sept
4.86 out of 5 average rating, 7 reviews