Guesthouse vacation rentals in Berkshire County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Berkshire County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Sheffield

5 out of 5 average rating, 12 reviews

Black Bear Bungalow, Sheffield Mass. U Will Love!

This private guest house with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts. Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house. The first level has a full size kitchen, living area with recliners and TV, large bath and laundry. Upstairs is a large bedroom with queen bed. This is a 2 person guest home.

Top guest favorite

Guesthouse in North Adams

5 out of 5 average rating, 263 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 272 reviews

Country Cabin

Lovely private country setting, air conditioner. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of request.) The space is for 2 adults but I'm flexible, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Guest favorite

Guesthouse in Stockbridge

4.92 out of 5 average rating, 25 reviews

Light-filled Carpenter's Cottage in Stockbridge

This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While it is a short distance away from our family home and one can hear the ambient hum of the highway, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. The cottage sleeps 2 in the queen sleigh bed, but there is seating for a dinner party of 6. It sits on a south-facing hill, looking out towards Monument Mountain. You’ll love it!

Top guest favorite

Guesthouse in Lee

4.95 out of 5 average rating, 74 reviews

Zen Berkshires Retreat - 4min to Stockbridge Lenox

Relax in this cozy, zen, modern 2bdrm guesthouse w/ private porch with sweeping views on historic property. Occasional wildlife sitings. Great location: Greenock Golf Course (1min Stockbridge center (4 min Lee Premium Outlets (5min Lenox center (9min Canyon Ranch (9min Kripalu (14min Austen Riggs (4min Near ski resorts: Bousquet (16 min Butternut (19 min Convenient to culture: The Mount (7min Shakespeare & Co (8min Norman Rockwell Museum (11min Tanglewood (11min Jacob's Pillow (17min

Top guest favorite

Guesthouse in Great Barrington

4.96 out of 5 average rating, 118 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Guest favorite

Guesthouse in Williamstown

4.93 out of 5 average rating, 238 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Guest favorite

Guesthouse in New Marlborough

4.9 out of 5 average rating, 198 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Guest favorite

Guesthouse in Lenox

4.93 out of 5 average rating, 365 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 227 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Guest favorite

Guesthouse in Stockbridge

4.91 out of 5 average rating, 127 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

Guest favorite

Guesthouse in Lenox

4.93 out of 5 average rating, 105 reviews

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.

0 of 0 items showing

What guests are saying

Hudson Valley and The Berkshires Cottage

4.76 out of 5 average rating, 33 reviews3 weeks ago

Ben was very friendly and responsive. It is hard to find a smaller but very nice accommodation in the Berkshires - this fit the bill. There were only two of us and we didn't need a 4-bedroom house, but we like nice places to stay and this surely fit the bill. The cottage is on two floors so affords some privacy and the house is well furnished by very uncluttered. We didn't use the kitchen but it was very nice and the bathroom was spacious and very nice.

Guesthouse in Hillsdale

What guests are saying

Romantic Berkshires cottage, great views, pool

4.88 out of 5 average rating, 40 reviews3 months ago

Clean and spacious one bedroom with kitchenette and full bath. Beautiful views of the neighboring farms and rolling hills through the many windows. Unit is located beneath a detached garage (walk out from unit to the backyard). Less than 10 mins to GB center, with easy access to nearby hiking trails. A nice place for a little getaway.

Guesthouse in Great Barrington

What guests are saying

Adorable 1 bedroom guesthouse in country setting.

4.73 out of 5 average rating, 37 reviews6 months ago

We were last minute guests and Michael and Jennifer were so gracious to let us stay. The mountain air and the occasional passing train made an idealic atmosphere. The cabin is surprisingly large and had everything we needed. Others have noted a wifi or cell service concern but that was not our experience. Thoroughly enjoyed our stay.

Guesthouse in Florida