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Search results; Over 1,000 homes in Chester

Top guest favourite
Home in Chester
Historic Mill • Near Okemo • Fireplaces • Wi-Fi
6 bedrooms, 9 beds, 3 private bathrooms
14–19 Jul
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5.0 out of 5 average rating, 104 reviews
Guest favourite
Home in Chester
Charming Chester Farmhouse Near VT Slopes
4 bedrooms, 4 beds, 1.5 bathrooms
5–10 Jul
4.88 out of 5 average rating, 97 reviews
Guest favourite
Hotel in Chester
Quaint Queen Room & Private Bath
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 47 reviews
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
New place to stay
Guest favourite
Cabin in Chester
Private Cabin 18mins from Okemo- "Pappy's Place"
3 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Chester
Luxe Rustic Cabin Near Okemo
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 74 reviews
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
20–25 Jul
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
Guest favourite
Home in Chester
4BR-4BA/Fireplace/Near Skiing/Walk to Shops
4 bedrooms, 8 single beds, 4 bathrooms
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cottage in Chester
Quaint stone house!
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.91 out of 5 average rating, 120 reviews
Guest favourite
Home in Chester
Historic 150-Year-Old Farmhouse | Jacuzzi included
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Jul
4.86 out of 5 average rating, 59 reviews
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
17–22 Jul
4.86 out of 5 average rating, 77 reviews
Top guest favourite
Home in Chester
Vermont Charm in the 1840 Gideon Lee House
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Chester
Modern 3BR/3BA Main+River Retreat | Ski Okemo
3 bedrooms, 6 beds, 3 bathrooms
1–6 Jul
5.0 out of 5 average rating, 8 reviews
Home in Chester
Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms, 5 beds, 3 bathrooms
1–6 Jul
4.84 out of 5 average rating, 45 reviews
Guest favourite
Home in Chester
Renovated 3-BR Cabin Near Okemo
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 5 reviews
Apartment in Ludlow
Ski-In/Ski-Out Luxury with Year-Round Resort Ame
2 bedrooms, 6 beds, 2.5 bathrooms
1–6 Jul
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
5–10 Jul
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Guest house in Chester
New in town Chester Retreat, 14 Miles to Okemo!
4 bedrooms, 6 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 21 reviews