Bed and breakfast vacation rentals in Berkshire County

Berkshire Hospitality and Comfort

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

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.

The Inn at Silver Maple Farm - Lower Lodge

The Lower Lodge is located on the ground floor and has a king-sized bed and a rustic Adirondack feel. The view overlooks the hillside and adjacent woods. A beautiful tree mural, wood bench, rocking chair, armoire with cable TV complete the Lower Lodge, which is located inside the Inn. A step-in shower (no bathtub) can accommodate a shower chair and also has a grab bar. This room can accommodate smaller sized wheelchairs; the doors are 35 inches wide, and the toilet is 18 inches high.

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.

Whistler's Inn/The Hunt Room (#4)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

Whistler's Inn/The Spanish Room (#1)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

Whistler's Inn/Mr. Whistler's Room (#7)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

Whistler's Inn/The Petite Chambre (#11)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

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.

The Cornell Inn Lenox

Escape to the charming Cornell Inn, a historic 28-room retreat in the heart of Lenox, MA. Nestled in the Berkshires, our inn blends New England charm with modern comforts. Enjoy cozy rooms, a delicious breakfast, and serene gardens. Just minutes from Tanglewood, hiking, and cultural attractions, it's the perfect getaway for relaxation and adventure. Experience warm hospitality in a timeless setting—book your stay today!

Superior Suite with a Patio Pets allowed

The Shaker Mill Inn is a unique family and pet friendly Inn that can be a comfortable and safe alternative to the traditional hotel and B&B. There is a self-check-in/check-out process. Each room has a private entrance, and is equipped with a kitchen or kitchenette, so that you can enjoy breakfast in the privacy of your room. The rooms and grounds are spacious, which will make for a relaxing visit to the Berkshires.

Petite space for a getaway

This bright and lovely bedroom with separate private bath is the perfect place to stay during your getaway to the Berkshires! We warmly welcome our guests to our safe, peaceful and centrally-located home in southeast Pittsfield. We have an additional suite in a different wing of the house as well. Guests are welcome to have a light continental breakfast in our kitchen from 7-9am.