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Compare 52 Cottages in Cheshire with updated reviews, rates, and availability.
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
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Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
10.0 out of 10, Exceptional, (1)
Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
10.0 out of 10, Exceptional, (1)
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
Berkshires - Charming Lakefront Cottage
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Seasonal lake front cottage with view of Burden Lake
Peaceful Seasonal lake front cottage with view of Burden Lake
10.0 out of 10, Exceptional, (2)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Cheshire
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (859)
The price is SAR 549
SAR 602 total
includes taxes & fees
12 Jum. II - 13 Jum. II
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1676)
The price is SAR 633
SAR 732 total
includes taxes & fees
12 Jum. II - 13 Jum. II
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Cheshire hotelsExpedia verified reviews
5/5 Excellent
"AC in the room was to noise. Other than that it was all good."
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 1 day ago
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