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

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.

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

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 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, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 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, this cabin is on the waterfront, a 1-minute drive from Pontoosuc Lake and 5 minutes from Onota Lake.

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.

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.