The Best Boutique Hotels in the Berkshires in 2026

On the border of Williamstown and North Adams, in a countryside that is a dream to drive around in, a roadside stop has a special type of appeal. Tourists Hotel is a newly-built, contemporary boutique hotel take on the theme, and it works beautifully. A lodge-style lobby and rooms that use wood grain as a decorative element strike a perfect balance of natural and design. With the Hoosic River in the backyard, you’ll enjoy Western Massachusetts’ gorgeous nature throughout your stay. The hotel property includes a suspension bridge that leads into… > Read Our Full Review

Imagine a 1970s Days Inn off Main Street, heading north out of Lenox, MA. Besides the obvious charm of Lenox, and the Berkshires, it might not sound that inviting. But put the building in the hands of hotel magicians Life House and they’ll make you reconsider what you thought you knew about roadside motels. When dressed up in retro furnishings and kitschy decor, the motel remodel can read a bit gimmicky, but Life House has taken this entirely seriously. The lobby and cocktail bar are impeccably decorated with a plush… > Read Our Full Review

Great Barrington may not be the heart of the Berkshires, but if you want a heaping slice of Americana with your gourmet breakfast, Granville House Hotel is the place. Whatever preconceptions you had about ‘mom and pop’ B&Bs, put them away. This boutique hotel inn, run by former managers of a top-tier roster of New York restaurants, offers world-class hospitality. This, complemented by an enchanting sense of home that could only be offered by a family living their dream, places Granville House a cut above even your Frette-linened luxury Inns…. > Read Our Full Review

This coven of boutique B&Bs populating the heart of Lenox, MA have perfected a harmonious blend of historical appeal and modern hospitality. You’ve got the classic farmhouse, the Whitlock, and the old tavern, the Dewey, both built in the 1700s. They both have centuries of stories that the Lenox collection is happy to tell. Our grandest option, the Constance, isn’t quite so old, but is the perfect selection for an inn, having hosted estate workers at the turn of the 19th century. It’s the face of the three, the check-in… > Read Our Full Review

Guess what kind of clientele this North Adams row of Victorians-turned-boutique hotel attracts? Did you guess art lovers? You’d be correct. It’s actually spitting distance from the area’s most famous art museum, the Massachusetts Museum of Contemporary Art, but we don’t recommend any spitting. It’s a cultured crowd, you see. Art lover or no, this Berkshires boutique inn is undeniably worth a visit. When else will you get to see such a street lined by identical Victorian townhouses? Each is painted slightly a different color though, so you know which… > Read Our Full Review