Bed and breakfast holiday rentals in Berkshire County

Beautiful Room in Hartfield House - The Berkshires

Hartfield House is a wonderful old home situated in the beautiful farming community of Sheffield Massachusetts, minutes from both the Catamount and Butternut ski resorts. We are only a few miles from the village of South Egremont and downtown Great Barrington, both with their share of amazing restaurants. We are in the heart of the Berkshire mountains, known for their lakes and trails, while also being close to Stockbridge, Tanglewood and numerous museums, galleries and points of interests.

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Sheffield Lodge - Ramblewood Master

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

Ground floor king bedroom in vintage farmhouse BnB

Wilder House Berkshires is a bed and breakfast located in the historic village of Sheffield. This ground-floor master bedroom is newly updated while preserving the charm of our 220-year-old farmhouse. Our lovingly designed common areas create fun and intimate opportunities for connection. Just 10 minutes from Great Barrington, the Berkshire School, Twin Lakes Connecticut, the Appalachian Trail, and epic waterfalls, our guests enjoy beautiful accommodations in a walkable village setting.

The Inn at Freeman Elms Farm B & B- Cottage Room

Our historic home was built in 1797 and has welcomed guests and family for over 200 years. Every room speaks to the history of New England and the town of Mill River. Included nearby are iconic venues of the Berkshires which include Gedney Farm, Butternut Ski Resort, the Appalachian Trail, Monument Mountain, Tanglewood, Jacob's Pillow, Barrington Stage Company, and Shakespeare and Company as well as little known, more local places such as Umpachene Falls and the Mill River Store.

Stockbridge #1 B&B Full Breakfast Close to Museums

The Stockbridge Country Inn the #1 Closest Berkshires Bed and Breakfast to the Norman Rockwell Museum, Chesterwood, and Botanical Gardens within walking distance. Nestled on four beautiful acres of lush landscape with lovely gardens surrounding an in-ground pool. Each of our luxury B&B Inn guest suites is tastefully appointed with private bath en suite, full bath amenities including soft cotton robes, and gourmet country style breakfast served daily.

Private Room and Bathroom - Clean, & Spacious

Hi, I'm Isla, This large bedroom has a Queen sized bed, a Sofa, TV, an Office’s desk and a private bathroom with shower. You will have use of the spacious kitchen and dining room area. The Townhouse is located in a cull de sac in a private community, so it is very quiet and safe. Includes a spacious, clean and bright kitchen fully stocked with pots, pans and utensils. Conveniently located close to everything the Berkshires has to offer.

The Inn at Silver Maple Farm - Loft Suite

Wood paneled cathedral ceiling, fireplace, and large sofa invite you to enjoy wrap-around views of both the hillside and gardens. Sunlight streaming in from windows on all four walls make this a very special and private retreat. After a day of exploring, come back and relax in your private soaking tub, and dream sweetly in a comfortable king-sized bed and a twin-sized futon bed. The Loft Suite has a TV with cable, and Wi-Fi.