The Best Hotels in Pittsfield

A 1960s motor lodge on the road between North Adams and Williamstown, now reborn as a boutique hotel with a decidedly hip second act. The Berkshires revival, fueled largely by MASS MoCA around the corner, gave someone the good idea to rescue this roadside relic rather than raze it. The result lands somewhere between nostalgia and design magazine, the kind of small country hotel that earns two Michelin Keys without making a fuss about it.

Named for George Bailey's house in "It's a Wonderful Life," this five-room bed and breakfast in Great Barrington is run by a couple who came up through the New York restaurant world. The rooms mix historical bones with modernist furniture and an eclectic haul of art and antiques. A billiards parlor and a music room keep things interesting between meals, and the Berkshires towns nearby handle lunch and dinner. Michelin has awarded it one Key.

A Victorian tavern turned 20-room boutique hotel on the edge of Lenox, where the rooms split the difference between antique atmosphere and working Wi-Fi. Some have reading nooks, some have private porches, all have local art on the walls. There's a living room for a drink, but no proper bar or restaurant, which is fine since the town center is a short walk and Stockbridge is minutes south. The Michelin Guide includes it among its selected hotels.

A Berkshires wellness resort where you can book a treetop ropes course in the morning and still order a cocktail before dinner, which puts it ahead of most places that use the word "wholesome" this often. The facilities are new, the design runs toward calm without tipping into cold, and the programming swings from spa treatments to beekeeping. It's an easy drive from New York, which the parking lot quietly confirms.

A 19th-century Italianate mansion on 22 acres of Olmsted-designed parkland, with 19 rooms and a French restaurant running eight tables. It is the kind of hotel that makes you wonder briefly if you've wandered into a novel. The Gilded Age bones are intact, the modern touches stay quiet, and Tanglewood is a short walk away for anyone who needs a reason to justify the room rate beyond sheer indulgence.

The kidney-shaped pool alone explains why someone brought a camera crew. The Springs Motel is a restored mid-century motor inn on Route 7 in the Berkshires, the kind of place that got a boutique makeover and then had that makeover filmed for TV. Cabins handle the larger groups, while the outdoor bar trailer and generous lawn keep everyone else occupied. It photographs well, and it holds up in person too.