Windsor Vacations

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.

Read less

Top Hotel Deals

See all Windsor hotels
1.0 out of 5 stars
1.5 out of 5 stars
2.0 out of 5 stars
2.5 out of 5 stars
3.0 out of 5 stars
3.5 out of 5 stars
4.0 out of 5 stars
4.5 out of 5 stars
5.0 out of 5 stars
Most popular package deals found by our travelers
Most popular package deals found by [originCity] travelers

Top Flight + Hotel Deals

See all Windsor packages

Top Deals on Flights

See all Windsor flights

Book a Vacation to Windsor