Bed and breakfast vacation rentals in Berkshire County

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Top-rated bed and breakfast rentals in Berkshire County

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Room in Williamstown

4.83 out of 5 average rating, 388 reviews

A Beautiful Home & Gardens In The Berkshires

The space is rented out to only one party at a time. Guests have their own entrance and bed and bathroom, which are upstairs, and both are separate from where my Mother and I live. There are three rooms, one has a queen, another has a double, and the third a 3/4 bed. The first bed is $125 per night and each additional bed is $60 per night. For parties of 4 - 6, there is another bathroom shower, toilet, and sink. The house is set off street and the surroundings are beautiful, quiet and safe.

Superhost

Room in Sandisfield

4.92 out of 5 average rating, 133 reviews

Hospitality in the Berkshire Woods

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!

Guest favorite

Room in Pittsfield

5.0 out of 5 average rating, 61 reviews

Two twin beds, first floor.

One of 4 bedroom listings in owner occupied home. This room is popular with travelers wanting separate beds or wanting to avoid stairs. It is located next to the first floor bathroom, which may be shared with the other first floor (“sunroom”) listing’s renter. Views of a lovely back yard with several garden beds. Shared kitchen, deck, living room. Park free. Centrally located, near Onota Lake and downtown Pittsfield. Lynette loves welcoming guests and orienting them to her beloved Berkshires.

Guest favorite

Room in Sheffield

4.97 out of 5 average rating, 30 reviews

Beautiful Hartfield House in 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.

Guest favorite

Nature lodge in Sheffield

4.98 out of 5 average rating, 43 reviews

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.

Room in Lee

4.95 out of 5 average rating, 40 reviews

Spacious King BR in Lee

Lg. King BR (new pillow-top) w/private bath, on 2nd floor of the house. 4 windows/view of pines, lg closet, ceiling fan, couch, desk, rocker. Central A/C. You may add 1-2 guests in 2nd BR (queen), sharing the bath, for $75 more. The 2nd BR will not be rented unless you rent it for your party. There is also a niche area on the 2nd floor with a refrigerator, microwave, coffeemaker, dining table. We provide breakfast items such as hard-boiled eggs, granola, yogurt, pastry, oj, coffee/tea, milk.

Guest favorite

Cabin in West Stockbridge

4.98 out of 5 average rating, 49 reviews

Modern Cabin near Tanglewood

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

Room in New Marlborough

5.0 out of 5 average rating, 14 reviews

The Inn at Freeman Elms Farm B&B- Harriot's 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 which include Gedney Farm, Butternut Ski Resort, the Appalachian Trail, the Normal Rockwell Museum, Jacob's Pillow, Barrington Stage Company, Berkshire School,and Shakespeare and Company as well as little know, more local places such as Umpachene Falls and the Mill River Store.

Guest favorite

Bed and breakfast in Lenox

5.0 out of 5 average rating, 11 reviews

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.

Room in Stockbridge

4.67 out of 5 average rating, 3 reviews

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.

Guest favorite

Farm stay in Williamstown

5.0 out of 5 average rating, 14 reviews

Scenic & Relaxing Farm Stay

Cobble Hill Farm is on the site of the nonprofit Education & Rescue Center. The 25 acre farm is an ideal location for families. The location brings lots of space to spread out and privacy all while being just a few miles to Williams College, Mass MoCA, and the Clark Art Institute. Swimming in the summer, a perfect sledding hill for winter and room for leisurely walks among 360 views of the foliage in the fall provide an escape from every day life.

Guest favorite

Room in Pittsfield

4.91 out of 5 average rating, 163 reviews

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.