An original historic inn from 1884 at the heart of a National Historic Landmark Village. Cozy guest rooms, pleasing amenities, AC, WiFi.

Charming, immaculate 11 rm B&B, all w/private bath, WiFi, frplce, A/C, full bkfst, family and group friendly, minutes to Tanglewood, Shaker Village, Hudson, Shakespeare and more.

Relax, restore, and explore from our fully-renovated mountain top lodge. Offering comfortable private guestrooms with outdoor firepits, hot tubs, and sauna. Every room has a stunning mountain view.

Formerly the Days Inn with 63 newly renovated rooms. Near Tanglewood, skiing, and Simon's Rock. Walk to downtown shops, theaters, and restaurants.

Old world charm modern amenities, 32 acres. Beautiful suites/pvt baths/heated pool/fireplaces/Jacuzzis/candlelit bkfst. #1 on Trip Advisor/Lee.

Restoration masterpiece-1885 schoolhouse. Exquisite suites w/frplcs and whrlpl baths. Spa rm w/jacuzzi for 2. Room dlvd. bkfst, king canopy beds.

Experience Gilded Age glamour, gourmet breakfasts, an outdoor heated pool and luxury accommodations in one of 14 elegant rooms or suites in the heart of the Berkshires.

Conceived and curated by home furnishings entrepreneur and Lenox resident, Annie Selke, 33 Main offers a delightful escape for the discerning traveler.

Lenox/Lee/Pittsfield - 130+ unique rooms and suites. 30 fireplace rooms, indoor pool, canopy beds, jacuzzis. Historic, romantic or extended stays. Groups welcome.

Doctor Sax House in Lenox, MA offers boutique luxury with elegant rooms, personalized service, and a lively atmosphere at their cafe and lounge, dulu.

Indoor pool. 96 rooms-some with fireplace, views, jacuzzis. Lounge, fitness, meeting space, free internet, continental breakfast. Groups, families, couples, corp welcome.

Award-winning hotel nestled on a wildlife preserve in the heart of the Berkshires. Smiles, cookies, free hot breakfast, and indoor pool are waiting to welcome you.

Concierge service, sumptuous breakfasts, comfortably elegant rooms. Close to Tanglewood, Lenox center and all attractions.

Gilded Age mansion, 27 acres of lush gardens for outdoor ceremony, grand ballroom, 57 bedrooms, ideal destination venue/professional event coordinator.

Restored Normandy-style barns with 16 guestrooms and suites. Granite fireplaces and whirlpool tubs. Exceptional wedding venue. Executive retreats.

Fine lodging and dining in elegantly restored stagecoach inn. Gracious rooms, AC, porches, fireplace, jacuzzis, TV. Serene gardens, pool, and views.

Retro décor with contemporary amenities across the street from MASS MoCA. European-style breakfast, bonfire, gazebo, EV Charging, Finnish-style sauna, outdoor hot tub, year-round heated outdoor pool, and state-of-the-art recording studio.

A stylish six room inn housed in a Georgian estate on twenty parklike acres.

Wilder House is a vintage inn in the historic village of Sheffield. 10 minutes from Great Barrington, the Berkshire School, and epic hikes, enjoy beautiful rooms in a walkable setting.

The Berkshires' rustic resort and cultural destination. Cozy trailside lodging, fireside dining, live music events, weddings, and retreats.

Landmark of hospitality. Antique filled rooms/suites. Three dining outlets: Main Dining Room, Tavern, Courtyard (seasonal). Banquet/event space. Live music on certain nights. Year-round pool and hot tub. Gift Shop.

Peaceful charm and elegance in a 1906 Georgian mansion on 12 acres. Delicious breakfasts, fireplace, heated pool, and more. A perfect backdrop for your wedding!

Idyllic and tranquil fully-furnished farmhouse on 4 acres. 5 bedrooms, 2 baths; sleeps 12. Screened porch overlooking gardens, stream, and wooded mountains.

Deluxe rooms at moderate prices. All have kitchenettes, private baths, TV, WiFi, AC, fireplace. Some with jacuzzi. Children/pets welcome. No smoking.

Where the modern world meets nature; 1948 Bauhaus design amidst 316 acres of open fields with spectacular views and four miles of hiking trails.