Bed and breakfast vacation rentals in Berkshire County

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Top-rated bed and breakfast rentals in Berkshire County

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Guest favorite

Room in Williamstown

4.83 out of 5 average rating, 387 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.

Dec 19 – 26

ﺩ.ﺇ492 per night

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.

Nov 1 – 8

ﺩ.ﺇ375 per night

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.

Jun 11 – 18

ﺩ.ﺇ748 per night

Guest favorite

Room in Pittsfield

4.99 out of 5 average rating, 375 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.

Apr 4 – 11

ﺩ.ﺇ385 per night

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.

Jul 21 – 28

ﺩ.ﺇ581 per night

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.

Jun 16 – 23

ﺩ.ﺇ564 per night

Guest favorite

Cabin in West Stockbridge

4.98 out of 5 average rating, 48 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.

Sep 11 – 18

ﺩ.ﺇ1,625 per night

Hotel in Lenox

5.0 out of 5 average rating, 4 reviews

Shadowbrook and Apple Tree Inn w/ Mountain View

Apple Tree Inn sits on 22 acres in the beautiful Berkshires. It has a seasonal outdoor swimming pool, free WiFi, a bar w/ live music, a restaurant, and complimentary European-style breakfast. No televisions available to encourage guests to enjoy the scenery. Tanglewood is a 10-minute walk. Please note that this room is above the bar. Guests staying here from Wednesday to Saturday may hear music until 11:00 p.m. Earplugs can be provided. Daily housekeeping can be accommodated for a fee.

Mar 13 – 20

ﺩ.ﺇ2,948 per night

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.

Jul 4 – 11

ﺩ.ﺇ941 per night

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.

Nov 7 – 14

ﺩ.ﺇ828 per night

Guest favorite

Farm stay in Williamstown

5.0 out of 5 average rating, 12 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.

Mar 15 – 22

ﺩ.ﺇ1,960 per night

Guest favorite

Room in Pittsfield

4.91 out of 5 average rating, 162 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.

Jun 14 – 21

ﺩ.ﺇ519 per night