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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Superhost

Private room in Sandisfield

4.93 out of 5 average rating, 138 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

Private room in Pittsfield

5 out of 5 average rating, 69 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

Private room in Sheffield

4.97 out of 5 average rating, 32 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.

Cabin in Sheffield

4.79 out of 5 average rating, 70 reviews

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.

Private room in Lee

4.95 out of 5 average rating, 41 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

Private room in Pittsfield

4.99 out of 5 average rating, 404 reviews

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.

Guest favorite

Cabin in West Stockbridge

4.99 out of 5 average rating, 74 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.

Guest favorite

Private room in Sheffield

4.97 out of 5 average rating, 74 reviews

Sheffield Lodge - Everett Room

Sheffield Lodge is a warm and inviting rustic Bed and Breakfast, secluded from the stressful city life, nestled in a forest of tall pines, maples, and birch trees. Enjoy your home-away-from-home where there is always welcoming hospitality, friendly service, and delicious breakfasts. Located just a short distance from the most popular activities and entertainment the Berkshires is known for including Tanglewood, Jacob's Pillow, skiing, stage theater, hiking, museums, and antique shopping.

Private room in New Marlborough

5 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

Private room in Lenox

4.94 out of 5 average rating, 18 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.

Guest favorite

Private room in Pittsfield

4.9 out of 5 average rating, 180 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.

Private room in East Chatham

5 out of 5 average rating, 4 reviews

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 queen futon bed. The Loft Suite has a TV with cable, and Wi-Fi.