Compare Cheap 5 Star Hotels

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, Hotel On North is a 1-minute drive from Barrington Stage Company and 7 minutes from Bousquet Ski Area.

With a stay at Holiday Inn Express & Suites Pittsfield - 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 Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.

Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.

With a stay at Berkshire Inn, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.

With a stay at Hilton Garden Inn Lenox Pittsfield in Pittsfield, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.

Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.

Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.

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

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 Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes by foot from Housatonic River.