Holiday rentals with outdoor seating in Williamstown

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.

Quality, Comfort, Charm in Williamstown Center

Stay at this completely renovated house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

Chic Downtown Studio, Perfect for College Weekends

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Bernie's & Betty's

Comfortably sleeping 6 with a large yard and screened-in porch, this charming 3-bedroom house is perfect for families looking for fun and adventure in the beautiful Berkshires. Minutes from Mass MoCA, Williamstown, and the Appalachian Trail, it is also an easy trip to Lenox (including Tanglewood) and other South Berkshire attractions. If you like the outdoors, you will love the easy access to ski slopes, hiking and biking trails. There is aTesla universal level 2 charger on the premises.

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana, our newest listing at Chase Hill Estate—the historic home of the owners of the factory that became MASS MoCA. More than just a house, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs at $100 per dog. My cottage sits on 13 privately owned acres. Partially fenced in 3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

COLD SPRING

Welcome to your peaceful Berkshire retreat. Originally a barn, this charming two-bedroom, one-bath apartment features a fully equipped kitchen, skylight-vaulted ceilings, and original wood beams. Just a short drive from Mount Greylock, Jiminy Peak, and the Williamstown Theatre Festival—surrounded by scenic hikes and great local dining, it’s the perfect home base for your getaway.