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Over 1,000 places in Cheshire

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Includes all fees, before taxes
Cottage in Cheshire
Entire Berkshires Lakehouse With Views
3 beds
Jun 1 – 6
$246 per night
Superhost
Home in Cheshire
19th c. Barn in The Berkshires
4 beds
Jun 11 – 16
$315 per night
Superhost
Cabin in Cheshire
Private Paradise in the Berkshires
1 bed
Jun 1 – 6
$155 per night
Superhost
Home in Cheshire
Berkshires Lakefront Retreat on 4 Private Acres
4 beds
Jun 14 – 19
$491 per night
Superhost
Home in Cheshire
Large home in Cheshire, near Ashuwillticook Trail
4 beds
Jun 1 – 6
$230 per night
Apartment in Adams
Park Street Twin Arches
1 sofa bed
Jun 1 – 6
$147 per night
Superhost
Home in Cheshire
Berkshire County Post-and-Beam Barn!
4 beds
Jun 1 – 6
$470 per night
Superhost
Home in Cheshire
Large Secluded Berkshire Home
5 beds
Jun 4 – 11
$343 per night, originally $388
Superhost
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
4 beds
Jul 29 – Aug 4
$348 per night
Superhost
Home in Lanesborough
Elmwood Farmhouse
6 beds
Aug 11 – 16
$272 per night
Superhost
Apartment in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
1 queen bed
Jun 13 – 20
$91 per night, originally $114
Superhost
Home in Cheshire
Berkshire County modern home + pool
5 beds
Jun 5 – 10
$490 per night
Superhost
Guest suite in Adams
Quaint Suite in Center of Adams
2 beds
Jun 1 – 6
$130 per night
Superhost
Tiny home in Florida
Off-Grid Tiny House
1 bed
Jun 11 – 16
$65 per night, originally $81
Apartment in Lanesborough
Charming Suite in 18th c. Berkshire Farmhouse
2 double beds
Jun 4 – 9
$111 per night
Superhost
Room in Lanesborough
Stay with Carlton
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
Jun 1 – 6
$100 per night
Superhost
31
Reviews
4.9
Rating
1
Year hosting
Cottage in Lanesborough
Wildlife Lakeside Cottage
4 beds
Jun 18 – 23
$285 per night
Cabin in Lanesborough
Glamping in the Berkshires w/ car charging station
7 beds
Jun 1 – 6
$350 per night, originally $397
Superhost