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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
6–11 Sept
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4.89 out of 5 average rating, 124 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, 51 reviews
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Chalet in Chester
Private 13-acre retreat, 20 min to Okemo
4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Sept
New place to stay
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Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.87 out of 5 average rating, 83 reviews
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Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
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Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
5–10 Nov
4.98 out of 5 average rating, 84 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
1–6 Sept
5.0 out of 5 average rating, 14 reviews
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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
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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
9–14 Sept
4.99 out of 5 average rating, 82 reviews
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Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Sept
4.87 out of 5 average rating, 62 reviews
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Superhost
Room in Chester
Tool Shed Cabin
1 bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Chester
Gorgeous VT Farmhouse, Dog Friendly!
4 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 31 reviews
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Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 107 reviews
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Superhost
Room in Chester
Milk House Cabin
1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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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
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Guest favourite
Shared room in Cavendish
YakPod #3 Snowed Inn Pod Lodge :12 min from Okemo!
1 bedroom, 1 bed, 1 shared bathroom
1–6 Sept
4.95 out of 5 average rating, 22 reviews
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Guest favourite
Home in Springfield
Historical Mansion Village View
6 bedrooms, 5 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 9 reviews