Walkable Berkshires Hotels in Lenox, Stockbridge & North Adams
Several Berkshires towns have centers compact enough to explore on foot. Lenox has shops and restaurants around Church Street, with Tanglewood and The Mount a short drive away. Stockbridge has the Red Lion Inn at the center of its village, Lee has Main Street inns, and Pittsfield's North Street has the Colonial Theatre. The properties in this collection sit in or next to those centers, so a car can stay parked for much of a stay.
10 Properties
TOURISTS
North Adams · Motel / Hotel
A former roadside motor lodge on the Hoosic River, rebuilt as a 46-room hotel on 80 wooded acres with trails, sculpture installations and a live music series. MASS MoCA is a few minutes away. TOURISTS Homes, a group of 19th-century houses in the neighboring Blackinton Historic District, opened in 2024 for longer stays.
The Porches Inn at MASS MoCA
North Adams · Inn
Forty-seven rooms in a row of restored Victorian row houses at 231 River Street, directly across the street from MASS MoCA, each house painted a different color. There is a four-season outdoor pool, an outdoor hot tub, a Finnish-style sauna and a fitness center, and breakfast is included in the daily amenity fee. The interiors mix eclectic decor with the original Victorian details, and dogs are welcome.
The Williams Inn
Williamstown · Inn
A 64-room inn on Spring Street in Williamstown, opened in 2019 in a stone-and-wood building modeled on New England farm architecture. The restaurant and bar, The Barn, is in a barn-style building on site. The Williams College Museum of Art is close by, and the Clark Art Institute is about a 10-minute walk.
Berkshires Untold
Lenox · Hotel / Motel
A 1970s roadside lodge at 194 Pittsfield Road on the north edge of Lenox, redesigned as a boutique hotel and now part of the Untold Collection; it was formerly Life House Berkshires. Rooms come in three types, from Classic Kings to Berkshires Suites, and some take dogs. The Club Room serves breakfast and has a bar, and the library lounge has floor-to-ceiling bookshelves and a fireplace.
Chambery Inn
Lee · Inn / B&B
A 19th-century parochial schoolhouse on Main Street in Lee, built in 1885 and converted into 9 rooms with the original blackboards still on the walls. Rooms have fireplaces, jetted tubs and canopy beds, with 8-foot windows and 13-foot ceilings, and breakfast is delivered to the door in a basket. Main Street's restaurants and shops are a short walk.
The Red Lion Inn
Stockbridge · Inn
An inn on Main Street in Stockbridge that has taken guests since 1773. It has 125 rooms, three restaurants, a year-round heated outdoor pool and live music in The Lion's Den. The rooms are furnished with antiques, and the birdcage elevator is still in use. The Norman Rockwell Museum is a short drive.
Hotel on North
Pittsfield · Hotel
A hotel in a converted 19th-century building on North Street in Pittsfield, the largest city in the Berkshires. There is an art gallery on the ground floor and a restaurant. Barrington Stage Company and the Colonial Theatre are nearby, and the location sits midway between north and south Berkshire County.
The Morgan House Inn
Lee · Inn
An inn at 33 Main Street in Lee, built in 1813 as a private home and opened to stagecoach travelers by Edwin Morgan in 1853. It has 11 rooms and a restaurant serving lunch and dinner, with a separate tavern menu. Ulysses S. Grant and George Bernard Shaw are among its past guests. Vern Kennedy has owned it since 2016, and Laurel Lake is a few minutes away.
The Dewey
Lenox · Inn / B&B
The Dewey, formerly the Birchwood Inn, has 11 rooms with fireplaces and antiques in the center of Lenox village, and is run by The Lenox Collection. The core of the house was built by Israel Dewey, one of the town's first settlers, and it hosted the first Lenox town meeting in 1767. Church Street's restaurants are a few minutes' walk away; Tanglewood, Jacob's Pillow and The Mount are a short drive.
Garden Gables
Lenox · Inn
A 16-room inn on Main Street in Lenox that reopened in April 2026 after a renovation of just under $1.4 million. The main house dates to 1780 and has been a hotel since 1951; rooms are split between it, a side building and 4 cottages. Check-in is digital and self-serve. Breakfast is not served on site; guests get nightly credits at partner restaurants in town. Guests must be 21 or older, and pets are not allowed.
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Browse Now →What Makes It
- •Lenox packs in a lot: the Tanglewood season in July and August, Shakespeare & Company, The Mount, Kripalu nearby, and enough restaurants for several nights without repeats. The Dewey and Garden Gables are both in the village.
- •In the north, The Williams Inn is about a 10-minute walk from the Clark Art Institute, and The Porches Inn faces MASS MoCA across River Street in North Adams.
- •Stockbridge is quieter and more historic — the Red Lion Inn is the anchor, and the town has a preserved village character that works for a night or two but is less suited to an extended stay than Lenox or Great Barrington.
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