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Search results; Over 1,000 homes in Chester

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Guest favourite
Cottage in Chester
Quaint stone house!
3 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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4.89 out of 5 average rating, 124 reviews
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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, 84 reviews
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Chalet in Chester
13-Acre Private Chalet | Game Room | Near Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
4.87 out of 5 average rating, 62 reviews
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Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.96 out of 5 average rating, 100 reviews
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Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 86 reviews
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Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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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
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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
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Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Chester
Modern Cabin | Near Okemo & Chester
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.85 out of 5 average rating, 46 reviews
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Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 165 reviews
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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
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Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 11 reviews
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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