Remote Berkshires Retreats & Country Inns
The Berkshires' reputation runs through its cultural corridor — Lenox, Stockbridge, Great Barrington — but the hills east of that corridor and the Hilltowns to the north have a quieter country that gets less attention. The remote Berkshires properties aren't trying to compete with the cultural circuit; they're for the trip where the point is the land. Properties in the Hilltowns between the Berkshires and the Pioneer Valley have a remove that the main tourist corridor doesn't offer at any price.
6 Properties
Guest House at Field Farm
Williamstown · Inn
Built in 1948 for modern art collectors Lawrence and Eleanor Bloedel, this five-room Bauhaus-influenced house sits on 300 acres of conservation land with views of Mount Greylock. The rooms are filled with original modern art and mid-century furniture — the collection is genuine, not decorative. Sculpture gardens, miles of trails, and downtown Williamstown a few minutes away. One of the most architecturally and artistically distinctive small properties in New England.
Wilder House Berkshires
Sheffield · Inn / B&B
A five-room B&B in Sheffield — one of the quieter and more genuinely rural towns in southern Berkshire County. Cooked-to-order breakfast on weekends, a fireplace in the lobby, and a location near Bartholomew's Cobble and the Appalachian Trail. Less discovered than the Lenox–Stockbridge corridor, with a corresponding price. The kind of property where the owner remembers you.
The Inn at Sweetwater Farm
Egremont · Inn / Farm
A working sheep farm and inn in the quiet hamlet of Egremont, near the New York border and the Catamount ski area. Eight rooms across an 18th-century farmhouse. Homemade breakfasts using farm eggs. The setting is genuinely rural in the southern Berkshires — no boutique signaling, no design moment. The kind of inn where people return the same week every year and the owners know why.
The Inn at Richmond
Richmond · Inn / B&B
A classic New England inn on 27 acres in Richmond — quiet, unhurried, with horses on the property and a breakfast program worth the morning. Equestrian setting with riding available. Between Pittsfield and the Connecticut border, well-positioned for anyone exploring the central Berkshires without paying the Lenox premium. The guests who find this place tend to come back.
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. Accessible by road or by through-hiking the Appalachian Trail. Private rooms and bunk rooms. Fieldstone fireplaces, arts-and-crafts furnishings, and views that justify the elevation. A Yankee Editors' Pick for Best Inn Landscape. One of the few places in New England where the inn itself is the destination, not an accessory to it.
Stonover Farm
Lenox · Inn / B&B
A three-room inn and two cottages on a working farm in Lenox — Kripalu-adjacent, quiet, and operating at a scale where the owners know every guest by name. The property has an organic garden, a pond, and direct access to walking trails. One of the smallest and most personal lodging options in the Berkshires, which is both the limitation and the appeal.
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Browse Now →What Makes It
- •The Berkshires' geographic range is wider than the cultural corridor suggests. The Hilltowns — Cummington, Chesterfield, Goshen — sit between the Berkshires and Springfield, and properties there are 30 minutes from the core but feel considerably more remote.
- •Several remote Berkshires properties offer significant private acreage: walking trails, ponds, meadows that function as a reason to stay on the property rather than driving to attractions. The land is the point.
- •The remote-Berkshires trip and the culture-Berkshires trip are genuinely different itineraries. Remote properties here work best for guests who want land and quiet rather than Tanglewood and museum-hopping.
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