filters

Search results; Over 1,000 homes in Chester

Photo 1 of 29
Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 beds, 1 private bathroom
7–12 Sept
,
5.0 out of 5 average rating, 39 reviews
Photo 1 of 27
Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 36 reviews
Photo 1 of 29
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
5–10 Oct
4.91 out of 5 average rating, 11 reviews
Photo 1 of 26
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms, 3 beds, 3 bathrooms
22–27 Sept
4.98 out of 5 average rating, 59 reviews
Photo 1 of 29
Top guest favourite
Home in Becket
Forest Home with Sauna
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Sept
4.94 out of 5 average rating, 34 reviews
Photo 1 of 29
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 49 reviews
Photo 1 of 29
Guest favourite
Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
4.98 out of 5 average rating, 47 reviews
Photo 1 of 29
Top guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
4.81 out of 5 average rating, 81 reviews
Photo 1 of 29
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
Photo 1 of 6
Top guest favourite
Room in Becket
Farmhouse Suite on Berkshire Farm
1 double bed, 1 bathroom
7–13 Sept
4.93 out of 5 average rating, 164 reviews
Photo 1 of 29
Top guest favourite
Flat in Otis
Enjoy every season the Berkshires have to offer.
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 132 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 151 reviews
Photo 1 of 27
Guest favourite
Home in Becket
Away from it all, close to everything
3 bedrooms, 3 queen beds, 2.5 bathrooms
10–15 Jan
4.94 out of 5 average rating, 16 reviews
Photo 1 of 29
Top guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
8–13 Sept
4.91 out of 5 average rating, 126 reviews
Photo 1 of 14
Top guest favourite
Cabin in Becket
Entire Private Log Cabin in the Berkshires
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 67 reviews
Photo 1 of 29
Guest favourite
Cabin in Becket
Tranquil Lake cabin with Kayaks
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
4.86 out of 5 average rating, 42 reviews
Photo 1 of 28
Top guest favourite
Cabin in Becket
Cozy Lake Side Cabin
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Photo 1 of 27
Top guest favourite
Home in Becket
Beautiful, quiet and cozy home in Becket!
3 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
4.94 out of 5 average rating, 154 reviews