Romantic Getaways in the Berkshires

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.

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.

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.

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.

Egremont · Inn

An inn in the village of North Egremont, about 4 miles from the center of Great Barrington, in an early-19th-century post-and-beam farmhouse. Every room has a private bath. Breakfast uses eggs from the inn's own hens and is open to the public by reservation. The inn is named for its artesian well water, and Baldwin Hill is within walking distance.

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.

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.

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.

Lee · Inn

A bed and breakfast for adults 21 and over, formerly the Inn at Laurel Lake, in a house built around 1904 with 500 feet of shoreline on Laurel Lake in Lee. Guests can swim from the property in summer and use the inn's kayaks and paddleboards, and there is a dock. Breakfast is included, and Tanglewood and Lenox are less than 10 minutes away.