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Cheshire

Welcome to Cheshire, a great destination to add to your next The Berkshires vacation.

Cheshire Vacation Packages

From Cheshire, Albany is 30 miles west, and Hartford is 60 miles southeast.

When the ocean breeze starts calling you, pack a bag and travel to Crystal Lake Sandy Beach, 60 miles away.

Nature lovers come to this part of the country to admire its marvelous natural landscapes. Experience the magic for yourself at Great Falls Discovery Center and Molly Stark State Park, 30 miles and 25 miles away from Cheshire, respectively.

Joseph L Bruno Stadium is 30 miles to the west of Cheshire. It's here you can watch the Tri-City ValleyCats play a home game. Notice the home team's colors of red, grey and white.

From hitting the slopes to building snowmen, ski resorts have something for the whole family. Cheshire is close to two, Mount Snow and Ski Sundown, merely 30 miles and 50 miles from the city.

Many vacationers recommend visiting St Mary's of the Assumption Church.

Albany International Airport is your closest airport at about 35 miles to the west, so make sure you give yourself plenty of time.


Top Hotel Deals

See all 118 Hotels in Cheshire
£112
Harbour House Inn

Harbour House Inn

725 North State Road, Cheshire
4.9
of 5, from 7 reviews
4.0 out of 5.0

Situated in the mountains, this bed & breakfast is within 6 miles (10 km) of Topia Arts Center, East Hoosac Quaker Meetinghouse and Susan B. Anthony Birthplace Museum. Mount Greylock and Western Gateway Heritage State Park are also within 9 miles (15 km).

£79
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.2
of 5, from 768 reviews
3.5 out of 5.0

Situated in Hancock, this condo is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 miles (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 miles (20 km).

£82
Cranwell Spa and Golf Resort

Cranwell Spa and Golf Resort

55 Lee Road, Lenox
4.1
of 5, from 97 reviews
4.0 out of 5.0

Situated in Lenox, this spa resort is within 2 miles (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum and Lenox Library. Shakespeare and Company and Wood's Pond are also within 3 miles (5 km).

£67
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.6
of 5, from 442 reviews
4.0 out of 5.0

Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary and Arrowhead Museum are also within 3 miles (5 km).

£73
Holiday Inn Berkshires

Holiday Inn Berkshires

40 Main St, North Adams
4.1
of 5, from 441 reviews
3.5 out of 5.0

Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library and Western Gateway Heritage State Park. Windsor Lake Park and Natural Bridge State Park are also within 2 miles (3 km).

£82
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.6
of 5, from 33 reviews
3.5 out of 5.0

Situated in Lenox, this hotel is within 2 miles (3 km) of Kennedy Park, Lenox Library and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 miles (5 km).

£76
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 346 reviews
3.0 out of 5.0

Situated in a rural location, this hotel is within 2 miles (3 km) of Arrowhead Museum, Kennedy Park and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 miles (5 km).

£78
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
4.7
of 5, from 84 reviews
3.5 out of 5.0

Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 miles (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 miles (5 km).

Top Deals on Flights

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