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Compare 59 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, (107)

Family-Friendly Richmond Cottage w/ Private Yard
Family-Friendly Richmond Cottage w/ Private Yard
10.0 out of 10, Exceptional, (4)

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)

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, (24)

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
10.0 out of 10, Exceptional, (1)

Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (3)

Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
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

19th c. Barn in the Berkshires
19th c. Barn in the Berkshires
9.6 out of 10, Exceptional, (85)

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1791)
The price is AED 437
AED 520 total
includes taxes & fees
24 Mar - 25 Mar

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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

The Williams Inn
5/5 Excellent
"Quality, tasteful decor and coffee/water station om each floor. Sitting/reading/game areas are very homey and super comfortable. Adding a self service microwave on each floor would be thoughtful. "
A verified traveler stayed at The Williams Inn
Posted 2 days ago
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