A more rustic alternative to the polish of Stockbridge and Lenox, Otis, with a ski area and 20 lakes and ponds, supplies plenty of what made the Berkshires desirable in the first place—the great outdoors. The dining and lodgings options here are slim; your best bet is to stay in Lee or Great Barrington and choose from among their tempting array of restaurants. Or head southwest to Old Marlborough and stay at the Old Inn on the Green (a circa-1760 B&B that began life as a stagecoach stop), where you can sample chef Peter Platt's swoon-worthy cuisine. Nearby Becket hosts the outstanding Jacob's Pillow Dance Festival in summer.