Remote Berkshires Retreats & Country Inns
Most Berkshires lodging is in the Lenox, Stockbridge and Great Barrington corridor. The properties here sit farther out. Bascom Lodge is at the 3,491-foot summit of Mount Greylock, the Guest House at Field Farm is on 316 acres of conservation land in Williamstown, and The Inn at Richmond has an equestrian facility near the New York line. In South County, The Inn at Sweetwater Farm in North Egremont and Wilder House in Sheffield are small farmhouse B&Bs.
6 Properties
Guest House at Field Farm
Williamstown · Inn
A 6-room guest house on Field Farm, a 316-acre property of The Trustees in Williamstown, with views of Mount Greylock. Lawrence and Eleanor Bloedel, collectors of modern art, built the house in 1948, and 13 sculptures stand on the grounds. More than 4 miles of footpaths cross the property, and The Folly, a 1965 cottage designed by Ulrich Franzen, is also on the land. Downtown Williamstown is a few minutes' drive.
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 Sweetwater Farm
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.
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.
Bascom Lodge
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.
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.
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Browse Now →What Makes It
- •Several of these properties have land of their own: Field Farm has more than 4 miles of footpaths, Stonover Farm has 10 acres with a spring-fed pond, and The Inn at Richmond has indoor and outdoor riding rings.
- •Bascom Lodge, a 1930s stone-and-timber lodge, sits where the Appalachian Trail crosses the summit of Mount Greylock, the highest point in Massachusetts.
- •A trip built around these properties is different from a Tanglewood weekend, though Stonover Farm, 0.7 miles from Tanglewood, manages both.
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