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Windsor Vacation Packages

Take a trip to Windsor, which you’ll find 25 miles (40 kilometers) to the north of The Berkshires. Coming from Albany International Airport in The Berkshires, Windsor is about 40 miles (64 kilometers) to the southeast.

Windsor is a popular place to visit while you are exploring The Berkshires as a large number of the area’s main attractions are nearby. Two destinations that should be at the top of every visitor’s list is the fascinating Mount Greylock and the much-loved Arrowhead Museum. Also, well worth the effort are Mass MoCA and the Hancock Shake Village.

To better understand The Berkshires, visit one of its museums and theaters. Experience a few of the popularater, dance and music performances at the Shakespeare and Company in Lenox and the Jacob's Pillow Dance. Head to the Williams College Museum of Art in Williamstown and the Sterling and Francine Clark Art Institute, to get your fix of art.

Head to the Prime Outlets Lee in Lee to scratch that shopping itch.

If you love sports, you might enjoy seeing local legends, the UMass Minutemen, take to the field at Mullins Center, Amherst. Make sure to wear maroon and white, the colors of the UMass Minutemen.

Finding somewhere comfortable to rest your head around the Windsor area is simple. Check out the rooms and rates at the Vacation Village in the Berkshires, Hancock, the Hampton Inn & Suites Berkshires Lenox, or the Jiminy Peak Mountain Resort, Hancock.


Top Hotel Deals

See all 116 Hotels in Windsor
£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).

£60
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
4.1
of 5, from 133 reviews
0.0 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 mi (10 km).

Top Deals on Flights

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