Great Barrington Massachusetts; Nestled in the heart of the Berkshire Hills along the beautiful Housatonic River is where you will find Great Barrington. The quintessential New England town with many homes and bed & breakfasts, rich in history and the social and shopping hub of the Southern Berkshires. Known for its summer culture, spectacular fall foliage, excellent skiing and of course its scenic beauty and out door activities, Great Barrington is a popular year round destination not to be missed. Known for its inns and bed and breakfasts, stays in one of the many well regarded inns/ bed and breakfasts is a great way to experience a relaxing Berkshire vacation in any season.