Lenox

The famed Tanglewood music festival has been a fixture in upscale Lenox for decades, and it's a part of the reason the town remains fiercely popular in summer. Booking a room here or in any of the nearby communities can set you back dearly when music or theatrical events are in town. Many of the town's most impressive homes are downtown; others you can only see by setting off on the curving, tortuous back roads that traverse the region. In the center of the village, a few blocks of shabby-chic Colonial buildings contain shops and eateries.