Berkshires Inns and Bed and Breakfasts: How the Towns Differ

Lee sits between Lenox and Stockbridge and has its own Main Street inns. The Morgan House Inn, a former stagecoach stop, has 11 rooms and a tavern. Chambery Inn is a 19th-century parochial school converted into 9 rooms.

Outside the center, Devonfield Inn has 11 rooms on 32 acres, with a heated seasonal pool and a tennis court, and Applegate Inn has 11 rooms and suites on a 6-acre estate across the road from a golf and tennis club. In this directory, most Lee inns fall in the lowest price tier, while most Lenox inns sit one tier higher. The Lee town page lists them all.

The Red Lion Inn has taken guests on Main Street in Stockbridge since 1773. It is much larger than a B&B, with three restaurants and a heated outdoor pool, at the center of the village. The Inn at Stockbridge is the smaller option, with rooms in a 1906 Georgian-style house, a cottage and a barn on 10 acres, about 2.4 miles from the Norman Rockwell Museum.

West Stockbridge is a smaller, quieter village a few miles west. Shaker Mill Inn has rooms with private entrances and kitchens or kitchenettes, which suit longer stays.

The towns around Great Barrington mix converted farm buildings with village inns. The Inn at Sweetwater Farm is an early-19th-century post-and-beam farmhouse in North Egremont, and breakfast uses eggs from its own hens. Gedney Farm in New Marlborough has 16 rooms and suites in a dairy barn built around 1906, on more than 50 acres, and its neighbor The Old Inn on the Green is a 1760 stagecoach stop with 11 rooms and a candlelit dining room.

Closer to town, ButtonBall Inn is a circa-1786 house in South Egremont with 12 rooms, renovated in 2025. Granville House in Housatonic has 5 rooms and received a MICHELIN Key in 2025, and Wilder House has 5 rooms in a Federal-style farmhouse in Sheffield, a short drive from the Appalachian Trail.

Northern Berkshire County has fewer small inns, but they sit close to the region's major art museums. The Guest House at Field Farm in Williamstown is a 1948 house with 6 rooms on 316 acres of conservation land, with views of Mount Greylock. The Williams Inn, with 64 rooms, is larger, and the Clark Art Institute is about a 10-minute walk away.

Southwest of Pittsfield, The Inn at Richmond has an equestrian facility with indoor and outdoor riding rings.

Summer demand in central Berkshire County follows the Tanglewood calendar. The festival runs from late June to around Labor Day; in 2026 it ran from June 21 to September 2, with the Boston Symphony Orchestra's concerts in the Koussevitzky Music Shed beginning July 10.

Minimum-stay rules vary by inn, and some set longer minimums for the festival. Hampton Terrace, for example, requires three nights on weekends from June 20 through Labor Day and two nights on other weekends. Inns with 5 to 15 rooms can fill well ahead of concert weekends and fall foliage, so it is worth checking a property's minimum-stay policy early.

The Berkshires bed and breakfast collection and the historic inns collection list the properties in this guide alongside the rest of the region.