For ridiculously easy access to MASS MoCA, book a room in one of the Porches Inn's six restored Victorians (from $125) located right across the street from the museum. A long wooden porch creaking with slat-back rocking chairs connects the buildings, once home to hundreds of mill workers (note the galvanized metal lunchboxes used for room service). Suites are decorated in so-called “industrial granny chic” (patchwork bedspreads, forties-era lamps, cushy armchairs) and share a heated outdoor pool that’s open for splashing all night long.
Ecoconscious from the bamboo floorboards to the solar-paneled rooftops, the brand-new Topia Inn (from $115) is the Berkshires’ first green B&B. Each of the inn’s ten rooms were designed by artist friends of the owners, a composer and dancer who also run the nearby Topia Arts Center. Both are situated on the scenic, eleven-mile Ashuwillticook Rail Trail, great for a morning walk capped by an aromatherapy shower back in your suite.
It was Whistler’s nephew, not his mother, who once lived in the 1820s English Tudor manor now known as Whistler’s Inn (from $160). Furnished with chandeliers, marble fireplaces, and a Steinway grand in the sitting room, the inn drips with old-world elegance—also ghosts. Three of them haunt the place, supposedly, and rooms five, seven, and twelve are said to be especially paranormally active.
Take a scenic chair lift to the summit of Jiminy Peak (from $99), where you can gawk at the 386-foot wind turbine installed earlier this summer. (It's the first of its kind at a North American mountain resort.) Though nothing fancy, the resort offers cheap, spacious, understated accommodations smack in the center of the Berkshires.