Search results; Over 1,000 homes in Chester

Superhost
Flat in Chester
Quiet getaway in the Berkshires
3 double beds
31 Aug – 5 Sept
₹54,785 for 5 nights
4.77 out of 5 average rating, 209 reviews
Top guest favourite
Home in Chester
Riverfront Getaway
2 queen beds
1–6 Sept
₹98,449 for 5 nights
4.97 out of 5 average rating, 351 reviews
Guest favourite
Room in Becket
Stay with Julia WilkinsJulia & robb retired,
East b.r. in upstairs suite of open plan home
16–21 Aug
₹38,258 for 5 nights
4.86 out of 5 average rating, 228 reviews
Guest favourite
Room in Becket
Stay with DonnaNurse,
Farmhouse Suite on Berkshire Farm
18–24 Aug
₹64,273 for 6 nights
4.93 out of 5 average rating, 154 reviews
Cabin in Chester
2 Rustic Cabins on 68 Secluded Acres
3 beds
1–6 Oct
₹1,12,426 for 5 nights
4.96 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 double beds
7–12 Sept
₹97,838 for 5 nights
4.95 out of 5 average rating, 286 reviews
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
3 beds
3–8 Sept
₹1,09,162 for 5 nights
4.98 out of 5 average rating, 40 reviews
Guest favourite
Campervan/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
2 beds
7–12 Sept
₹42,339 for 5 nights
4.89 out of 5 average rating, 185 reviews
Top guest favourite
Guest house in Cummington
Clark Cottage
2 beds
5–10 Oct
₹74,882 for 5 nights
5.0 out of 5 average rating, 114 reviews
Guest favourite
Flat in Otis
Enjoy every season the Berkshires have to offer.
2 beds
24–29 Aug
₹73,965 for 5 nights
4.95 out of 5 average rating, 109 reviews
Home in Huntington
Historic Huntington Home - Walk to Westfield River
5 beds
24–29 Aug
₹97,073 for 5 nights
4.17 out of 5 average rating, 36 reviews
Top guest favourite
Room in Easthampton
Stay with MarthaRetired appraiser,
Martha's on Main
17–22 Aug
₹48,460 for 5 nights
4.99 out of 5 average rating, 96 reviews
Guest favourite
Room in Chicopee
Stay with AmeliaHosting for 11 years,
Botanical Room, Queen bed, shared bath
29 Aug – 3 Sept
₹27,036 for 5 nights
4.9 out of 5 average rating, 153 reviews
Guest favourite
Cabin in Becket
Cozy Cottage in the Woods
4 double beds
17–22 Aug
₹77,250 for 5 nights
4.91 out of 5 average rating, 23 reviews
Casa particular in Hinsdale
Berkshire Lake-side "Glamping"
4 beds
15–20 Aug
₹55,775 for 5 nights
New place to stay
Top guest favourite
Home in Washington
Peaceful Retreat in the Berkshires
4 beds
9–14 Sept
₹1,02,735 for 5 nights, originally ₹1,20,877
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Becket
Forest Home with Sauna
6 beds
2–7 Sept
₹1,42,420 for 5 nights
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Room in Northampton
Stay with LaniI am a bodyworker.,
Third Beautiful Bedroom
4–9 Sept
₹38,768 for 5 nights
5.0 out of 5 average rating, 18 reviews