Photo by Ed Gaffny
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Compare 60 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, (104)
Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (13)
Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (22)
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)
15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake
15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake
10.0 out of 10, Exceptional, (8)
Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
6.0 out of 10, (1)
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.
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Other property types in Cheshire
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1750)
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (920)
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (200)
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 hotels
Recent reviews of Cheshire hotels
5/5 Excellent
"Super friendly front desk staffs. We had wonderful time. "
A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites
Posted 1 day ago