Compare Cheap Hotels in Cheshire

With a stay at Hotel Downstreet, an Ascend Collection Hotel, you'll be centrally located in North Adams, a 1-minute drive from Massachusetts Museum of Contemporary Art and 15 minutes from Green Mountain National Forest.

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.

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.

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

When you stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.

When you stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of National Shrine of the Divine Mercy and Norman Rockwell Museum.

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-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 Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.

Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.

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