The Berkshires - especially Pittsfield, Lenox, Stockbridge, W. Stockbridge are fabulous places to visit. Allow at least a week to experience everything from amazing lakes (Onata, Pontoosic) where beaches are free and hiking/picnic availability abounds. The waters are pristine and families can spend the day without any expense.
Shopping in each town is fun, boutique sized and artsy.
Explore the wide range of concerts at Tanglewood, or a spa/yoga experience at Kripalu - Lenox. (Set on the mountainside- awesome programs for any age or ability or desire of program). Very green- and excellent organic/vegetarian buffet food.
A wide range of accomodations- including state park camping- or high end B & B. Be ready for a celebrity sighting ! As folks like James Taylor kayaking across a lake is not unusual.
A relaxing, sophisticated, down to earth, fun loving area- each Berkshire town offers a huge array of things to do. Excellent travel bargain- and WOW- scenic wonder.
Just get there! "You've got a friend- in the Berks !" Our family visits at least monthly! Love it.