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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
29 Aug – 3 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Room in Becket
Farmhouse Suite on Berkshire Farm
1 double bed, 1 bathroom
31 Aug – 6 Sept
4.93 out of 5 average rating, 162 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
23–28 Aug
4.87 out of 5 average rating, 261 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
23–28 Aug
4.91 out of 5 average rating, 171 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Room in Hadley
The 1797 House/Locke bedroom along CT River
2 beds, 1 bathroom
19–24 Sept
4.83 out of 5 average rating, 398 reviews
Guest favourite
Cabin in Becket
Cozy Cottage in the Woods
2 bedrooms, 4 double beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 42 reviews
Cottage in Becket
Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 289 reviews
Top guest favourite
Room in Agawam
Hampshire Room
1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 324 reviews
Guest favourite
Cottage in Otis
The lake house
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Tower in Amherst
The Silo | Next to UMass & open farmland/ nature
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Rooms in Holyoke
Two Sunny Rooms in Country Setting
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Room in West Springfield
Luxurious spacious suite in a home.
1 bed, 1 bathroom
21–26 Aug
4.89 out of 5 average rating, 72 reviews
Top guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 163 reviews