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Cheshire

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

Packages in Cheshire

Booking both your flights and a place to stay is really simple with Expedia. Booking your desired flights and accommodations are the ingredients for a good vacation. Combining them together with us into a single package deal is a recipe for success that takes out the stress and saves you money. That means added cash for your Cheshire trip!

Receive savings of up to 17% by securing a package deal.

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Check out some of the best prices ever at Expedia and book the trip you've been pondering. Your family will thank you for it.

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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.

Accommodation in Cheshire

Cheshire lodging options could be limited. Be sure to book ahead with Expedia to find the right room for you.

The Spring's Inn and Topia Inn - An Organic Oasis are the main accommodation options in and around Cheshire.


Top Hotel Deals

See all 130 Hotels in Cheshire
£105
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).

Harbour House Inn B&B

Harbour House Inn B&B

725 North State Road, Cheshire
3.5 out of 5.0

Situated in Cheshire, this bed & breakfast is in the same area as Topia Arts Center, Mount Greylock State Reservation Visitor Center and Susan B. Anthony Birthplace Museum. Area attractions also include East Hoosac Quaker Meetinghouse and Mount Greylock.

£73
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.2
of 5, from 796 reviews
3.0 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).

£111
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
4.0
of 5, from 508 reviews
3.5 out of 5.0

Located in the mountains, this Hancock condominium resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and within 16 mi (25 km) of Waubeeka Golf Links and Canoe Meadows Wildlife Sanctuary. New Lebanon Library and Mount Lebanon Shaker Village are also within 12 miles (20 km).

£56
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.9
of 5, from 498 reviews
3.0 out of 5.0

Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 miles (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. Lenox Library and Bousquet Ski Area are also within 3 miles (5 km).

£80
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.5
of 5, from 48 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).

£71
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 354 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).

£56
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
4.1
of 5, from 442 reviews
3.0 out of 5.0

Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and Berkshire Museum are also within 6 miles (10 km).

Top Deals on Flights

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