Family-friendly vacation rentals in Williamstown

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.

Charming Williamstown Cottage

This beautifully restored small home in the heart of Williamstown is the perfect location for visitors to the attractions of the Berkshires. Walk to the theater, shopping, restaurants, Williams College campus and Sterling and Francine Clark Art Institute. A king master bedroom, 2 twins in the second upstairs bedroom, a full sized futon in the 3rd bedroom and a queen sleeper sofa provides sleep for 7-8 in total. All the amenities one might need for a comfortable stay are here for you!

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Charming Farmhouse Apt Near Williams College

Relax in this charming New England farmhouse apartment just minutes from Williams College, Mass MoCA, and downtown Williamstown. This private second-floor retreat features original wood floors, a spacious bedroom with a comfortable queen bed, a fully equipped kitchen, and a peaceful setting perfect for couples, Williams College visitors, and Berkshire escapes. Enjoy easy access to local restaurants, hiking trails, museums, and the best attractions throughout the Berkshires.

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 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, 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.

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.

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!

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

Cozy barn apartment on the river

Private converted first floor barn apartment next to the Green River. Comfortable with unique furnishings and back door that opens to a riverfront covered patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper, tri-fold floor mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. It is on our property with a shared driveway.

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.

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.