2 Best, Genuine Boutique Hotels in Lenox in 2026

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

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