filters

Search results; Over 1,000 homes in Chester

Photo 1 of 25
Guest favourite
Cottage in Chester
Quaint stone house!
3 bedrooms, 3 beds, 1.5 private bathrooms
6–11 Sept
,
4.89 out of 5 average rating, 124 reviews
Photo 1 of 20
Guest favourite
Hotel in Chester
Private Suite in Historic Inn
1 bedroom, 2 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 83 reviews
Photo 1 of 16
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
Photo 1 of 29
Chalet in Chester
Where GOOD TIMES Live on
4 bedrooms, 6 beds, 3.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 12
Barn in Chester
1850's converted barn apartment in Chester
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Photo 1 of 29
Guest favourite
Home in Chester
Okemo Valley Chalet
5 bedrooms, 13 beds, 2.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 29
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, 85 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 17
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
Photo 1 of 6
Top guest favourite
Room in Chester
Farm at Williams River House - Hawthorne Suite-ADA
1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 28 reviews
Photo 1 of 6
Top guest favourite
Room in Chester
Farm at Williams River House - Essex Suite
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 44 reviews
Photo 1 of 29
Guest favourite
Home in Springfield
Historical Mansion Village View
6 bedrooms, 5 beds, 4.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Guest favourite
Home in Chester
Luxury, Historic home easy drive to ski areas.
6 bedrooms, 8 beds, 3 bathrooms
3–8 Sept
5.0 out of 5 average rating, 25 reviews
Photo 1 of 29
Home in Chester
Serenity Now Farmhouse | Peaceful Country Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Photo 1 of 29
Top guest favourite
Barn in Andover
Fat Cat Barn - Close Okemo & Magic, Vermont
5 bedrooms, 10 beds, 2.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 154 reviews
Photo 1 of 28
Top guest favourite
Home in Chester
Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
2 bedrooms, 4 beds, 2 bathrooms
7–13 Sept
4.96 out of 5 average rating, 98 reviews