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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
29 Aug – 3 Sept
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4.86 out of 5 average rating, 144 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Cabin in Chester
Thistle House Glamping Retreat w/ Hot Tub + Sauna
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 82 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 96 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.87 out of 5 average rating, 82 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
24–29 Aug
4.85 out of 5 average rating, 46 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.93 out of 5 average rating, 165 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.87 out of 5 average rating, 62 reviews
Guest favourite
Home in Chester
Spacious Historic Stone Home near 4 Ski Mountains
5 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 111 reviews
Guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 106 reviews
Superhost
Home in Ludlow
Downtown | Hot Tub, Speakeasy, GameRoom, Fireplace
6 bedrooms, 7 beds, 2.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Ludlow
The Evergreen Chal-A
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Cabin in Ludlow
Sunny Summer Cabin | Scenic Views + Deck
3 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
4.98 out of 5 average rating, 65 reviews