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Search results; Over 1,000 homes in Chester

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Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
3 bedrooms, 3 beds, 2 private bathrooms
2–7 Aug
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4.86 out of 5 average rating, 140 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
4.97 out of 5 average rating, 77 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
4.86 out of 5 average rating, 78 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
4.99 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
4.85 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Barn in Chester
1850's converted barn apartment in Chester
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4.87 out of 5 average rating, 60 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Aug
Home in Chester
Okemo Valley Chalet
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 13 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
4.96 out of 5 average rating, 90 reviews, 2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
4.93 out of 5 average rating, 164 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Ludlow
The Evergreen Chal-A
5.0 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4.96 out of 5 average rating, 74 reviews, 4 bedrooms, 6 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Plymouth
Charming pet-friendly retreat in the Vermont woods
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Guest suite in Chester
Stone Village Private Studio
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Tiny home in Ludlow
Alpine Reflection + Hot Tub
4.96 out of 5 average rating, 102 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Aug – 1 Sept
Guest favourite
Home in Andover
Mountain Retreat | Hot Tub | 9 Acres | Views
5.0 out of 5 average rating, 29 reviews, 4 bedrooms, 7 beds, 2 bathrooms
1–6 Aug