15 Best Hotels in The Berkshires, Massachusetts

Tucked away in a wooded glen a short distance from Tanglewood, this cozy 1880s inn often has classical music playing in the fireplace-lighted library; the breakfast room, overlooking the glen, serves afternoon tea with homemade scones on weekends. Guest rooms have antique furnishings, romantic style, and, in some, fireplaces, wicker rocking chairs, and tiled bathrooms; the carriage house offers a pair of handicap-accessible rooms.

A converted 19th-century country schoolhouse houses these unique accommodations in downtown Lee where the cavernous guest rooms—some big enough for two queen beds—maintain their schoolhouse roots with blackboards still hanging on their walls. Rooms are decorated in French style and have 13-foot embossed ceilings and state-of-the-art baths. There are no common rooms, so breakfast baskets are delivered to your room each morning.

Massive stone fireplaces in the lobby and lounge lend this hotel a ski-lodge atmosphere—suites in the building's rear overlook the slopes—and the condo-style suites (privately owned but put into a rental pool) can accommodate up to four people. All units have couches and kitchenettes separated from living areas by bars with high stools, and are also equipped with Wi-Fi and flat-screen TVs—if you want to ski Jiminy Peak, you won't find anything more convenient.

Occupying a grand Federal house from 1800, the Devonfield sits atop a birch-shaded hillside overlooking 32 acres of rolling meadows, and offers elegant but not ostentatious guest rooms that deftly blend Colonial style (four-poster beds, working fireplaces, some Oriental rugs) and modern convenience (Wi-Fi, flat-screen TVs, and in some cases whirlpool tubs). The innkeepers' attention to detail manifests itself in numerous ways, from the chocolates in your room and a guest pantry that is always open, to the rotating menu of homemade breakfasts.

Once the 1912 summer cottage of Harley Procter (as in, Procter & Gamble), this beautifully updated country inn has guest rooms and suites in various configurations and styles; most have working fireplaces, detailed moldings, and plush carpeting. The restaurant, which offers late-night dining in summer, was a favorite hangout of painter Norman Rockwell in the days before the gorgeous piano bar and its comfortable seating were installed.

Built in 1948, this guesthouse contains a fine collection of art on loan from Williams College and the Whitney Museum, as well as lobby that wouldn't be out of place on a 1960s movie set. Guest rooms feature private decks and expansive views of Mt. Greylock and the 315-acre property; two rooms have working tile fireplaces. Both property and clientele are upscale and fancy, which is probably why children under 12 are not permitted.

Although it's near Route 2 and surrounded by parking lots, this thoroughly proper hostelry compensates with a courtyard filled with fruit trees and a pond stocked with koi, which the inner guest rooms look out onto; outer rooms with fireplaces are more appealing in winter. The spacious accommodations are furnished with English antiques, comfortable beds, and deluxe linens.

Around the corner from Mass MoCA and Main Street, these Victorian mill-workers' houses dating to the 1890s have been restored and are connected with one long porch and some interior hallways walled with exteriors of the old houses to become one of New England's quirkiest hotels. Rooms—some can sleep up to six—have a mix of retro 1940s and 1950s lamps and bungalow-style furnishings, along with stunning bathrooms with slate floors, hot tubs, and mirrors fashioned out of old window frames.

Listed on the National Register of Historic Places, this 1770 Georgian Colonial is a rustic place to discover simpler times. Guest rooms are sprinkled with antique pieces—washstands, wing chairs, and spinning wheels—and some have wide-plank walls, curtains of unbleached muslin, and four-poster or rope beds.

Antique furnishings accent the guest rooms of this comfortable 1906 Georgian Revival inn, where each of the spacious and airy rooms has a decorative theme, such as Kashmir, Provence, or the Berkshires. Innkeepers serve breakfast in the elegant dining room, and provide wine and cheese every evening, where you can overlook the beautiful grounds.

An inn since 1773, the Red Lion has hosted presidents, senators, and other celebrities, in the large and historic main building filled with antiques and small guest rooms. If you don't care about authentic ambience or prefer more space and modern furnishings, request a room in one of the annexes.

Step back in time and sleep comfortably in one of the fun, retro rooms or plan a weekend away with a group of friends or family at the cabins that can sleep up to six Magnolia Network fans will recognize this newly renovated hotel's owner Lindsey Kurowski, who bought and renovated the roadside motel on the second season of her show Inn the Works.

Innkeepers Nana Simopoulos and Caryn Heilman have transformed a derelict downtown building into an eco-friendly marvel, with solar panels and natural clay walls. Guest rooms are decorated in themes ranging from Ancient Greece to Native American, with bedding and linens made from organic cotton and all-natural toiletries in the bathrooms; some rooms have steam showers or spa tubs with colorful "chromatherapy" lights, so you can enjoy a little light show as you bathe.