Bed & Breakfasts in the Berkshires
Eleven bed and breakfasts in the Berkshires, most of them in Lenox and Lee. Lenox has four, including The Dewey in the center of the village and Stonover Farm, 0.7 miles from Tanglewood. Lee, about 10 minutes away, has three, and in this directory most Lee inns sit in a lower price tier than most Lenox inns. The rest are in Stockbridge, Richmond, Sheffield and Housatonic. Most have between 5 and 15 rooms, and five have pools.
11 Properties
Hampton Terrace Inn
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.
Brook Farm Inn
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.
Devonfield Inn
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.
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.
Inn at Stockbridge
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.
Granville House
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.
Wilder House Berkshires
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.
The Inn at Richmond
Richmond · Inn / B&B
An inn on State Road in Richmond with rooms, suites and cabins, on land whose history the inn traces to 1776. A full-service equestrian facility on the property has indoor and outdoor riding rings. Continental breakfast is served on weekdays, and the inn's chef cooks a brunch on weekends. Richmond is southwest of Pittsfield, near the New York line.
Applegate Inn
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.
Stonover Farm
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.
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.
How to Choose
Stonover Farm
For the shortest trip to Tanglewood
Five suites and cottages on 10 acres, 0.7 miles from Tanglewood. The main house was built in 1890 for New York lawyer John E. Parsons, and breakfast is cooked to order in the Creamery, which overlooks a spring-fed pond.
The Dewey
For staying in Lenox village
Eleven rooms with fireplaces and antiques in a 1760s house in the center of Lenox, where the town's first meeting was held in 1767. Church Street's restaurants are a few minutes' walk.
Hampton Terrace Inn
For a pool near downtown Lenox
Fourteen rooms on Walker Street, a 5-minute walk from downtown, with a seasonal heated pool and a breakfast buffet. The owners live on site. Weekends from June 20 through Labor Day have a three-night minimum.
Brook Farm Inn
For a lower price in Lenox
Fifteen rooms in an 1882 house on a side street, most with fireplaces, and a heated pool in spring and summer. The inn keeps a poetry library and has hosted readings by poets including Galway Kinnell and Philip Levine. It is in this directory's lowest price tier, unlike most Lenox inns.
Chambery Inn
For the building
Nine rooms in an 1885 schoolhouse on Main Street in Lee, with the original blackboards still on the walls and the high ceilings intact. Rooms are large by B&B standards, and Main Street's restaurants are a short walk.
Devonfield Inn
For grounds and a pool
A Federal-style main house on 32 acres between Lenox and Stockbridge, with rooms, suites, a cottage and carriage-house units. There is a seasonal heated outdoor pool, two hiking trails and a fire pit, and the upgraded rooms have fireplaces and whirlpool tubs.
Applegate Inn
For a Georgian mansion with a pool
A 1920s Georgian mansion on 6 acres, half a mile from the center of Lee, with 11 units: rooms and suites in the main house and carriage house, and a 2-bedroom cottage with a kitchen. Many rooms have fireplaces and whirlpool tubs, there is a heated pool, and a public golf course and tennis courts are across the road.
Inn at Stockbridge
For a 1906 estate
A Georgian-style mansion built in 1906 and run as an inn since 1982, on 10 acres at the edge of Stockbridge, with rooms in the Main House, the Cottage House and the Barn. There is a seasonal pool, a bar and lounge and a fitness room, and the Norman Rockwell Museum is about 2.4 miles away.
The Inn at Richmond
For riding
An inn in Richmond, southwest of Pittsfield near the New York line, with a full-service equestrian facility and indoor and outdoor riding rings. It has rooms, suites and cabins, with a continental breakfast on weekdays and a brunch on weekends.
Wilder House Berkshires
For a small house in South County
Five rooms in an 1802 house on Sheffield's Main Street, near Bartholomew's Cobble and the Appalachian Trail. Breakfast is made to order, and rates run below those in the Lenox–Stockbridge corridor.
Granville House
For a MICHELIN Key stay
Five rooms on Division Street in Housatonic, run by Terry and Terri Coughlin, veterans of the New York restaurant world, and named for George Bailey's house in It's a Wonderful Life. Rooms mix antiques with modernist furniture, and the inn received a MICHELIN Key in 2025.
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Browse Now →What Makes It
- •Lenox has four of the eleven. The Dewey has 11 rooms in a 1760s house in the village center, and Hampton Terrace, with 14 rooms, is a 5-minute walk from downtown. Stonover Farm is 0.7 miles from Tanglewood.
- •Lee has three: Chambery Inn's 9 rooms are in an 1885 schoolhouse on Main Street, and Applegate and Devonfield, outside the center, both have heated pools.
- •Three are very small, with 5 rooms or suites each: Stonover Farm, Wilder House and Granville House. Tanglewood and foliage weekends fill early, and some inns set multi-night minimums at those times.
- •Breakfast styles differ. Stonover Farm and Wilder House make breakfast to order, Hampton Terrace sets out a buffet, and The Inn at Richmond serves a continental breakfast on weekdays and a brunch on weekends.
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