8 Best Hotels in The Berkshires, Massachusetts

This restored building in the center of town mixes original brickwork and hardwood with tasteful modern decor to provide spacious accommodations and common spaces, including a large horseshoe bar. The staff is as attentive to guests as they are to the history of the property, which creates a very welcoming atmosphere.

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.

This minimalist hotel has many oak-covered surfaces, a large fireplace in the rustic lobby, amazing views of Mt. Greylock from the patio deck and courtyard, and walking trails that lead guests to a suspension bridge, sound sculpture, and a restaurant. Guest rooms all have a window nook to curl up in, and a TV, desk, minibar, and radio, but otherwise lack extras, including phones.

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.

Built in 1948, this guesthouse contains a fine collection of art on loan from Williams College and the Whitney Museum, as well as a 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.

Located just behind the Adams Theater and steps away from the paved Ashuwillticook Rail Trail, this newly remodeled inn is a hidden spot for art and nature lovers just 10 minutes from downtown North Adams. The inn uses only organic materials and offers guest packages with discounts for the nearby theater.