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Search results; Over 1,000 homes in Chester

Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 77 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
12–17 Aug
4.86 out of 5 average rating, 78 reviews
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
New place to stay
Top guest favourite
Cabin in Chester
Thistle House at Camp Greenwood Vermont with Sauna
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.99 out of 5 average rating, 81 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
4.85 out of 5 average rating, 46 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Aug
4.87 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
4.96 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 164 reviews
Top guest favourite
Cabin in Ludlow
Cozy Ski Cabin | 5 minutes to Okemo
4 bedrooms, 6 beds, 1.5 bathrooms
1–6 Aug
4.96 out of 5 average rating, 74 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Ludlow
Breathtaking Mountain View & Walk To Town
4 bedrooms, 6 beds, 2 bathrooms
3–8 Aug
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
3 bedrooms, 6 beds, 1.5 bathrooms
3–8 Aug
4.95 out of 5 average rating, 320 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
Apartment in Ludlow
Main St Escape | Explore Downtown Ludlow
2 bedrooms, 3 beds, 1 bathroom
5–10 Aug
4.99 out of 5 average rating, 147 reviews
Top guest favourite
Home in Ludlow
The Evergreen Chal-A
3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Ludlow
Private Mountain House with hot tub and A/C
3 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 31 reviews