Compare Cheap 5 Star Hotels

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.

When you stay at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood in Stockbridge, you'll be next to a golf course, within a 5-minute drive of Berkshire Botanical Garden and Norman Rockwell Museum.

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Lenox Arts Center.

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 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.

With a 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 Tanglewood Music Center and Housatonic River.

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