Guesthouse holiday rentals in Berkshire County

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Top-rated Guesthouses in Berkshire County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Lenox

4.93 out of 5 average rating, 390 reviews

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 20-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Top Guest favourite

Guesthouse in North Adams

5 out of 5 average rating, 279 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 favourite

Guesthouse in Becket

4.93 out of 5 average rating, 275 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.

Top Guest favourite

Guesthouse in Williamstown

4.97 out of 5 average rating, 67 reviews

Ritz-Carlton Bed * Walk to Williams * Steam Sauna

Welcome to the Mt. Williams Retreat—a centrally located, design-forward wellness guesthouse just two blocks from Williams College. This thoughtfully appointed love letter to the Berkshires offers luxury amenities including: 🧖‍♀️ Steam sauna and shower room 🛏️ Ritz-Carlton mattress topped with plush hotel linens ☕ Breville automatic café machine with complimentary coffee and teas 🌿 Private garden patio with seasonal water feature 🪟 Cathedral windows and ceilings 🔥 Radiant floor heating

Guest favourite

Guesthouse in Stockbridge

4.94 out of 5 average rating, 35 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!

Guest favourite

Guesthouse in Great Barrington

4.95 out of 5 average rating, 134 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 favourite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 202 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 favourite

Guesthouse in Williamstown

4.93 out of 5 average rating, 243 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse 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 favourite

Guesthouse in Stockbridge

4.95 out of 5 average rating, 239 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.

Top Guest favourite

Guesthouse in Tyringham

5 out of 5 average rating, 7 reviews

The Little House: A Cozy Cottage Guest House

Cozy cottage guest house nestled in the countryside. This tiny house is perfect for a couple or the solo traveler looking to escape into the tranquility of the beautiful Berkshires. Close to all of the modern conveniences and yet tucked away, we are minutes from the Appalachian Trail, on a historic property that once hosted Mark Twain for two summers. Kick back and relax in this calm, clean, stylish space.

Guest favourite

Guesthouse in Stockbridge

4.9 out of 5 average rating, 139 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 favourite

Guesthouse in Lenox

4.94 out of 5 average rating, 109 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.