Barn / Ranch

Cottage Farm of the Berkshires

📍382 Churchill St, Pittsfield, Massachusetts, 01201

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.

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.

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.

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 Red Lion Inn

📍30 Main St, Stockbridge, Massachusetts, 01262

Storied inn with nearby guesthouses offering turndown service, a heated pool & farm-to-table dining.

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.