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Search results; Over 1,000 homes in Chester

Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Room in Becket
Farmhouse Suite on Berkshire Farm
1 double bed, 1 bathroom
10–15 Sept
4.93 out of 5 average rating, 164 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
9–14 Sept
4.87 out of 5 average rating, 265 reviews
Top guest favourite
Cabin in Becket
Cozy Cottage in the Woods
2 bedrooms, 2 double beds, 1 bathroom
9–14 Sept
4.91 out of 5 average rating, 44 reviews
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
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, 155 reviews
Home in Middlefield
Cozy Berkshires home with brook & sugar house
3 bedrooms, 3 beds, 1 bathroom
15–20 Sept
New place to stay
Guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 265 reviews
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 51 reviews
Superhost
Home in Becket
Lake front retreat - Stylish Berkshire home
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.92 out of 5 average rating, 180 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 Sept
4.98 out of 5 average rating, 267 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Northampton
Light filled three bedroom apartment DT Florence!
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 492 reviews
Top guest favourite
Cabin in Becket
Cozy Lake Side Cabin
2 bedrooms, 3 beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 311 reviews
Top guest favourite
Home in Otis
Idyllic family retreat - spacious lake home,
4 bedrooms, 5 beds, 2.5 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 175 reviews
Guest favourite
Cabin in Otis
Berkshires Cedar Cabin: complete privacy
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 13 reviews