Historic Inns of the Berkshires

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.

Lenox · Inn

A 12-room inn on Walker Street in Lenox, built in 1912 as the summer estate of Harley Procter, of Procter & Gamble, to a design by McKim, Mead & White. Rooms mix king and queen beds, fireplaces and sitting areas. The restaurant serves dinner, with live piano music on some nights. Past guests include Arthur Fiedler and Norman Rockwell.

Lenox · Inn / B&B

A 14-room inn on Walker Street in Lenox, a 5-minute walk from downtown. There is a seasonal heated pool, and breakfast is a buffet with dishes like pancakes, French toast and frittatas. The owners live on site. Weekend stays have a three-night minimum from June 20 through Labor Day, and Tanglewood is a few minutes' drive.

Lenox · Inn / B&B

A 15-room inn in an 1882 house on a side street in Lenox, known for its library of poetry, history and literature and for the poets it has hosted for readings, including Galway Kinnell and Philip Levine. Most rooms have a fireplace, and there is a heated outdoor pool in spring and summer. Tanglewood is a short drive.

Lenox · Inn

A Gilded Age manor on 27 acres on Plunkett Street in Lenox, next to Edith Wharton's estate, The Mount. Its 56 rooms are split between the historic manor and a newer motel wing. A breakfast buffet is included, and there is a pool. Rates run below those of its immediate neighbors on the same road.

Lee · Inn / B&B

A bed and breakfast on 32 acres between Lenox and Stockbridge, in a Federal-style main house first built in the early 1800s. Lodging includes rooms, suites, a cottage and carriage house units, and the upgraded rooms have fireplaces and whirlpool tubs. There is a seasonal heated outdoor pool, two hiking trails and a fire pit, and breakfast includes a cold buffet and a choice of hot dishes.

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.

Lee · Inn

Fifty-two rooms on Laurel Lake at 435 Laurel Street in Lee, with kayak and pontoon boat rentals, beach access and an exercise room. Mint, an Indian restaurant, overlooks the water, and some rooms take dogs. Rates sit in the middle of the range for a corridor where Tanglewood-season prices run high. It is part of Choice Hotels' Ascend Collection.

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.

Stockbridge · Inn / B&B

A Georgian-style mansion built as a private residence in 1906 and run as an inn since 1982, on 10 landscaped acres at the edge of Stockbridge. Rooms are split between the Main House, the Cottage House and the Barn. There is a seasonal pool, a bar and lounge and a fitness room, and a hot breakfast is included. Some rooms take pets. The Norman Rockwell Museum is about 2.4 miles away.

West Stockbridge · Inn

A suite-style inn at 2 Oak Street in the village of West Stockbridge, near the Massachusetts Turnpike. Every room has a private entrance and a kitchen or kitchenette, check-in is self-serve, and families and pets are welcome. Wine and snacks are included, there is a fire pit, and work by Berkshire artists hangs throughout. Tanglewood's main gate is a short drive.

Housatonic · Inn / B&B

A 5-room inn on Division Street in Housatonic, run by Terry and Terri Coughlin, veterans of the New York restaurant world. It is named for George Bailey's house in Frank Capra's It's a Wonderful Life. Rooms mix antiques and modernist furniture with an eclectic art collection. Granville House received a MICHELIN Key in the 2025 guide.

New Marlborough · Inn

A 1760 stagecoach stop at the center of the historic village of New Marlborough. Eleven rooms have working fireplaces, antique furniture and claw-foot tubs. The dining room is lit only by candles, and chef-owner Peter Platt's seasonal menu is open to diners who aren't staying the night. Gedney Farm is next door.

New Marlborough · Inn / Farm

An inn on more than 50 acres of pasture and meadow in New Marlborough, with 16 rooms and suites in a dairy barn built around 1906, with its original post-and-beam frame. Many rooms have granite fireplaces and whirlpool tubs, and most standard and fireplace rooms take pets. The property also hosts weddings and events.

Sheffield · Inn / B&B

A 5-room B&B in an 1802 house at 48 South Main Street in Sheffield, a rural town in southern Berkshire County, run since 2023 by Brad Sanzenbacher and Jamee Herbert. Breakfast is made to order. Bartholomew's Cobble and stretches of the Appalachian Trail are nearby, and Great Barrington is about 10 minutes north. Rates run lower than in the Lenox–Stockbridge corridor.

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.

Adams · Lodge

A 1930s Civilian Conservation Corps stone-and-timber lodge at the 3,491-foot summit of Mount Greylock, the highest point in Massachusetts. It can be reached by road or on foot by the Appalachian Trail, which crosses the summit. There are private rooms and bunk rooms, fieldstone fireplaces and Arts and Crafts furnishings.

Lee · Inn / B&B

An 11-unit inn in a 1920s Georgian mansion with white columns at 279 West Park Street in Lee, on a 6-acre estate half a mile from the center of town. The main house has 5 rooms and 3 suites, and the carriage house has 2 suites and a 2-bedroom cottage with a kitchen. There is a heated pool, many rooms have fireplaces and whirlpool tubs, and a public golf course and tennis courts are across the road.

Lenox · Inn / B&B

A 5-unit inn on 10 acres in Lenox, 0.7 miles from Tanglewood. Three suites are in the main house, built in 1890 for New York lawyer John E. Parsons, with 2 more in Rock Cottage and The School House. It opened as an inn in 2002 and has been owned since 2021 by Randy Grimmett and Allison Smith. Breakfast is cooked to order and served in the Creamery, overlooking a spring-fed pond, and there is a bar and a library for guests.

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.

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.

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.

South Egremont · Inn

A 12-room inn on Main Street in South Egremont, about 2 miles from Great Barrington. The main house was built around 1786 and has taken guests since the 1940s under several names, the last being The Egremont Village Inn. New owners renovated it in 2025. ButtonBall Kitchen, the inn's restaurant, opened in 2026 to guests and the public, and The Barn, a live music venue, is on the property. Pets are welcome.