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Cheshire Vacation Packages

Spend a while in Cheshire, which is 25 miles (40 kilometers) to the north of The Berkshires. Coming from Albany International Airport in The Berkshires, Cheshire is 35 miles (56 kilometers) to the southeast.

Cheshire is within easy reach of a diverse collection of The Berkshires’s more popular attractions. Mount Greylock and Mass MoCA are just two of the popular places to visit. Two other popular spots that are located within a short distance of Cheshire are the Sterling and Francine Clark Art Institute and Hopkins Observatory.

Cheshire offers some interesting cultural attractions within easy reach that allow visitors to really get a feel for the area. Learn, admire and be thoroughly entertained in the various museums including Arrowhead Museum in Pittsfield. The area is a great destination for art lovers. Don’t miss the Williams College Museum of Art in Williamstown.

To make sure you get the most out of Cheshire, think about making a reservation at one of the area’s charming bed and breakfast or hotel options. The Vacation Village in the Berkshires, Hancock, the Jiminy Peak Mountain Resort, Hancock and the Howard Johnson Williamstown are just three of the best places to find a warm welcome and a good night’s rest.


Top Hotel Deals

See all 114 Hotels in Cheshire
£95
Harbour House Inn

Harbour House Inn

725 North State Road, Cheshire
5.0
of 5, from 3 reviews
3.5 out of 5.0

Situated in the mountains, this bed & breakfast is within 6 mi (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 mi (15 km).

£76
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.1
of 5, from 238 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 mi (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 mi (20 km).

Rose and Goat Retreat

Rose and Goat Retreat

9 Moores Rd, North Adams
4.0 out of 5.0

Located in the mountains, this family-friendly resort is within 9 mi (15 km) of Windsor Lake Park, Natural Bridge State Park, and Mass MoCA. North Adams Public Library and Western Gateway Heritage State Park are also within 9 mi (15 km).

1896 House Brookside & Pondside Country Motels

1896 House Brookside & Pondside Country Motels

910 Cold Spring Rd, Williamstown
4.2
of 5, from 10 reviews
0.0 out of 5.0

Situated in a rural location, this bed & breakfast is within 3 mi (5 km) of Williamstown Historical Museum, 62 Center for Theater and Dance, and Chapin Library of Rare Books and Manuscripts. Williams College Museum of Art and Williams College are also within 3 mi (5 km).

£86
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.7
of 5, from 16 reviews
3.0 out of 5.0

Situated in Lenox, this hotel is within 2 mi (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 mi (5 km).

Cavalier Cottage B&B

Cavalier Cottage B&B

236 East Oxbow Road, Shelburne Falls
3.0 out of 5.0

Situated in the mountains, this cottage is within 6 mi (10 km) of Salmon Falls, Bridge of Flowers, and Bissell Covered Bridge. Berkshire East Ski Resort and Hail to the Sunrise Statue are also within 9 mi (15 km).

£51
Super 8 Lee/Berkshires/Outlet Area

Super 8 Lee/Berkshires/Outlet Area

170 Housatonic Street, Lee
3.5
of 5, from 74 reviews
2.0 out of 5.0

Situated in Lee, this motel is within a 15-minute walk of Lee Prime Outlets, Lee Library, and Animagic Museum of Animation. Greenock Country Club is 0.9 mi (1.4 km) away.

£87
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
3.8
of 5, from 145 reviews
3.0 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 mi (20 km).

Top Deals on Flights

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