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Get away to romantic Cheshire! Enjoy the skiing, hiking and natural setting.

Venture to sights like Mount Greylock State Reservation as you discover the local area in Cheshire.

Harbour House Inn
Harbour House Inn
3.5 out of 5
725 North State Road, Cheshire, MA
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Situated in the mountains, this bed & breakfast is 1.7 mi (2.8 km) from Mount Greylock State Reservation and within 6 miles (10 km) of Topia Arts Center and ...
4.8/5Exceptional! (19 reviews)
"Very friendly, welcoming and personal. Breakfast was outstanding."

Reviewed on 2 Sep 2019

Harbour House Inn
Ski at 19th c. Renovated Barn in the Berkshires
Ski at 19th c. Renovated Barn in the Berkshires
195 W Mountain Rd, Cheshire, MA
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Situated in Cheshire, this holiday home is 1.2 mi (2 km) from Mount Greylock State Reservation and within 6 miles (10 km) of Topia Arts Center and East Hoosac ...
4.8/5Exceptional! (32 reviews)
A Gem In The Berkshires
"My husband and I headed to the Berkshires for a few days of cross-county skiing and snowshoeing before the arrival of spring. The accommodations were perfect! The renovated barn is welcoming and hearth-centered. The craftsmanship on the restoration is detailed and the furnishings quite comfortable. ..."

Reviewed on 20 Mar 2021

Ski at 19th c. Renovated Barn in the Berkshires
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Hancock, MA
Free cancellationReserve now, pay when you stay
The price is £83 per night from 22 Apr to 23 Apr
Situated in Hancock, this condo is 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort and within 6 miles (10 km) of Mount Greylock State Reservation and Pittsfield ...
4.2/5Excellent! (1,320 reviews)
"The room was a great price and you have your own mini apartment!"

Reviewed on 13 Apr 2021

Vacation Village in the Berkshires
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.
Ski at 19th c. Renovated Barn in the Berkshires
Ski at 19th c. Renovated Barn in the Berkshires
195 W Mountain Rd, Cheshire, MA
Situated in Cheshire, this holiday home is 1.2 mi (2 km) from Mount Greylock State Reservation and within 6 miles (10 km) of Topia Arts Center and East Hoosac ...
4.8/5Exceptional! (32 reviews)
A Gem In The Berkshires
"My husband and I headed to the Berkshires for a few days of cross-county skiing and snowshoeing before the arrival of spring. The accommodations were perfect! The renovated barn is welcoming and hearth-centered. The craftsmanship on the restoration is detailed and the furnishings quite comfortable. ..."

Reviewed on 20 Mar 2021

Ski at 19th c. Renovated Barn in the Berkshires
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
The price is £102 per night from 21 Apr to 22 Apr
Located in the mountains, this Hancock condominium resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center ...
4/5Very Good! (699 reviews)
"niece place for winter vacation"

Reviewed on 10 Feb 2021

Jiminy Peak Mountain Resort
Honeysuckle Rose Cottage
Honeysuckle Rose Cottage
173 Barker Rd, Pittsfield, MA
Situated in Pittsfield, this holiday home is within 2 miles (3 km) of Colonial Theater, Berkshire Museum and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary ...
4.5/5Wonderful! (2 reviews)
Quaint and Beautiful Little Cottage
"We loved staying here! It was quaint and relaxing, just what we wanted. Despite the age of the cottage the heaters throughout kept us nice and warm. We were cozy the whole time. Some great books to read on the shelves and the TV was set up with streaming services and cable. Not a far drive from trails ..."

Reviewed on 11 Mar 2021

Honeysuckle Rose Cottage
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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