Guesthouse holiday rentals in Berkshire County

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.

Light-filled Carpenter's Cottage w/ EV charger!

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. EV charger! The cottage sleeps 2 in the queen 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!

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.

Modern barn in the heart of the Berkshires

Modern, renovated 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. Family and pet friendly! *Please read Interaction with Guests section before booking*

The Carriage House: Spotless, Charming 2 Bedroom

The 1820 Carriage House is in the heart of the beautiful Berkshires. Williamstown and Mass MoCA are up the road, Lenox is to the south, and Mount Greylock is around the corner. It's a fully equipped 950 square foot cottage, light, airy, charming and immaculate, conveniently located in Lanesborough. With seven rooms, two stories, a comfy queen and full-sized bed, full kitchen, washer/dryer and off-street parking, your Berkshire visit will be as comfortable as it is memorable.

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 House in Stockbridge 3 miles to Tanglewood

A bike ride to downtown Stockbridge and 3 miles to Tanglewood and Kripalu.. Located in the Historic Interlaken section of Stockbridge. One bedroom guesthouse attached to 1829 colonial. One bedroom with queen bed and actual 100% cotton sheets from Pottery Barn. Living area with beautiful view of Larrywaug brook, full size pull out couch with 100% cotton sheets. Bath has shower-no tub. Equipped kitchenette. NO STOVE. 10 Miles to Great Barrington.

Bitty Berkshire Bungalow

Just 2 miles from historic Stockbridge's Red Lion Inn, 1 mile from the Norman Rockwell Museum and the Berkshire Botanical Garden, 15 minutes from Bosquet ski resort, 12 minutes from Tanglewood, and around the corner from Chesterwood, in the lush forest of Massachusetts' Berkshire mountains, this cozy "bitty bungalow" is the perfect place from which to foray out on wonderful adventures in this vacation wonderland, returning for quiet rest and renewal.

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.

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 House at Stonover Estate

Located on historic Estate grounds, this is an aesthetically pleasing and private getaway for adults and couples. The town of Lenox hosts multiple 5-star restaurants, and the property is a 10 minute walk to town. It is 1 mile from Tanglewood, 1 mile to Shakespear & Co., and 14 miles to Jacob’s Pillow. If you like the outdoors, it is a half mile to Kennedy Park for hiking or biking.

Guest House 15 mins to Tanglewood

Studio guesthouse is all yours. In a quiet valley near walking and hiking trails. Close to Tanglewood, the Stockbridge Bowl, and Kripalu. 10 minutes to downtown West Stockbridge and No. 6 Depot Roastery and Cafe. 15 minutes to Great Barrington. The guest house is on owner's property and there is a dog on the premises. Absolutely no pets or children under 18.