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 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.

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.

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.

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.

When you stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

With a stay at Pocketbook Hotel and Bath in Hudson, you'll be within a 15-minute drive of Olana State Historic Site and Oakdale Beach.

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.

With a stay at The Wick, Hudson, A Tribute Portfolio Hotel in Hudson, you'll be within a 15-minute drive of Olana State Historic Site and Max and Lillian Katzman Theater.