Hotel & Resort
Devonfield Inn
📍85 Stockbridge Rd, Lee, Massachusetts, 01238
Refined rooms & suites in a charming B&B offering free cognac, gardens & a seasonal outdoor pool.
Barn / Ranch
Cottage Farm of the Berkshires
📍382 Churchill St, Pittsfield, Massachusetts, 01201
Hotel & Resort
The Inn at Stockbridge
📍30 East St, Stockbridge, Massachusetts, 01262
Polished rooms & suites in a 1906 mansion with an outdoor pool, plus free wine & cheese socials.
Hotel & Resort
Hampton Terrace Inn
📍91 Walker St, Lenox, Massachusetts, 01240
Posh B&B in a Victorian mansion offering elegant rooms, an outdoor pool & complimentary liqueurs.
Hotel & Resort
Chambery Inn
📍199 Main St, Lee, Massachusetts, 01238
Elegant, French-inspired rooms & suites in a 19th-century schoolhouse offering free breakfast.
Barn / Ranch
Brook Farm Inn
📍15 Hawthorne St, Lenox, Massachusetts, 01240
Bright rooms in a quaint B&B offering a heated outdoor pool, a library & regular afternoon tea.
Barn / Ranch
The Guest House at Field Farm
📍554 Sloan Rd, Williamstown, Massachusetts, 01267
Modern art-filled B&B featuring hiking trails, a sculpture garden & an outdoor pool.
Venue
Bloom Meadows
📍2422 Hancock Rd, Williamstown, Massachusetts, 01267
Hotel & Resort
Stockbridge Country Inn
📍26 Glendale Rd, Stockbridge, Massachusetts, 01262
B&B in a garden setting featuring antique-filled rooms, a fireside lounge & an outdoor pool.
Venue
TOURISTS
📍915 State Rd, North Adams, Massachusetts, 01247
Chic quarters, most with forest views, in a tranquil lodge offering an outdoor pool & dining.
Barn / Ranch
Stonover Farm
📍169 Under Mountain Rd, Lenox, Massachusetts, 01240
Elegant, 19th-century B&B offering polished suites & cottages, as well as a courtyard & a patio.
Ballroom
Barrington Hall
📍426 Stockbridge Rd, Great Barrington, Massachusetts, 01230
Garden
Berkshire Botanical Garden
📍5 W Stockbridge Rd, Stockbridge, Massachusetts, 01262
15 acres of flower beds, ponds & gardens for strolling & picnicking, plus exhibits & events.
Barn / Ranch
Canyon Ranch Lenox
📍165 Kemble St, Lenox, Massachusetts, 01240
Posh resort centered around a stately mansion, offering health-conscious dining & an expansive spa.
Hotel & Resort
The Porches Inn at MASS MoCA
📍231 River St, North Adams, Massachusetts, 01247
Eclectic quarters in a boutique hotel with a heated pool, a hot tub & a sauna, plus free breakfast.
Venue
Blantyre
📍16 Blantyre Rd, Lenox, Massachusetts, 01240
Elegant quarters in a posh property offering a spa, a restaurant & a pool, plus tennis courts.
Hotel & Resort
The Black Swan Lee - Lenox, an Ascend Collection Hotel
📍435 Laurel St, Lee, Massachusetts, 01238
Warmly decorated rooms in a woodsy hotel offering an informal restaurant with lake views.
Hotel & Resort
The Red Lion Inn
📍30 Main St, Stockbridge, Massachusetts, 01262
Storied inn with nearby guesthouses offering turndown service, a heated pool & farm-to-table dining.
Resort
Miraval Berkshires Resort and Spa
📍55 Lee Rd, Lenox, Massachusetts, 01240
Venue
Berkshires Untold
📍194 Pittsfield Rd, Lenox, Massachusetts, 01240
Hotel & Resort
THE 1896 House Inn and Country Lodgings
📍910 Cold Spring Road, Route 7, 910 Cold Spring Rd, Williamstown, Massachusetts, 01267
Quaint, old-world country hotel set in a 19th-century property offering a pool & a restaurant.