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Compare 70 Cottages in Cheshire with updated reviews, rates, and availability.

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

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

Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (13)

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)

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

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)

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
10.0 out of 10, Exceptional, (9)

Lake Views & Dock Access - Pittsfield Cottage!
Lake Views & Dock Access - Pittsfield Cottage!
10.0 out of 10, Exceptional, (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, (1792)
The price is SAR 446
SAR 531 total
includes taxes & fees
14 Apr - 15 Apr

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (925)
The price is SAR 503
SAR 552 total
includes taxes & fees
5 Apr - 6 Apr

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (240)
The price is SAR 563
SAR 859 total
includes taxes & fees
10 Apr - 11 Apr
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
"Nicest place in Williamstown. Excellent restaurant. Very comfortable room."
A verified traveler from Boston stayed at The Williams Inn
Posted 2 days ago
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