Compare Cheap Hotels in Windsor

With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.

Located in Lenox, The Yankee Inn is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.

With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.

Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Cheshire Reservoir.

Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.

With a stay at Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG in Pittsfield, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.

With a stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Housatonic River.

With a stay at Red Roof Inn PLUS+ South Deerfield – Amherst in South Deerfield, you'll be within a 15-minute drive of University of Massachusetts Amherst and Yankee Candle Village.

With a stay at Howard Johnson by Wyndham Lenox in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.

Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.

With a stay at Hotel Downstreet, an Ascend Collection Hotel, you'll be centrally located in North Adams, within a 15-minute drive of Green Mountain National Forest and Western Gateway Heritage State Park.

Located in Hancock, Jiminy Peak Mountain Resort is in the mountains, within a 15-minute drive of Mount Greylock State Reservation Visitor Center and Waubeeka Golf Links.