16 Best Hotels in The Berkshires, Massachusetts

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.

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.

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.

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. Innkeepers serve breakfast in the elegant dining room, and provide wine and cheese every evening, where you can overlook the beautiful grounds.

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.

As a third-floor B&B above retail frontage, the Barrington may lack the exterior aesthetic appeal of its Berkshire peers, but it more than compensates for this by its central Main Street location and spacious, eclectically furnished guest rooms. All rooms have queen beds, pull-out sofas, and inviting sitting areas.

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.

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 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.

This 380-acre resort underwent a $130 million renovation and name change, transforming the former Cranwell Resort into a more polished, high-end Miraval property. A renewed focus on health and wellness means guests are given access to golfing, spa packages, yoga and fitness classes, equine programming, and nutrition counselling. This is an all-inclusive experience, with large rooms, plenty of activities, a world-class spa and dining options that are included in the price of your stay. Miraval is less about experiencing the Berkshires and more about your own mental and physical health journey within the property's offerings. 

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.

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.  

Located in the heart of Williams College territory, this newly remodeled inn will be tough to book on parent or alumni weekends, but it's worth a try. It's slightly larger than your typical inn, but does still embrace nature with outdoor firepit seating, and a lighted walkway to help you walk to downtown easily.