Family-friendly holiday 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.

Steps to MoCA Near SKI: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

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.

Currently being renovated for a fresh modern 2026

BRAND NEW Kitchen and Bathroom to be completed December 2025. Stay tuned! Enjoy old unit pricing until updated photos are published. Second floor 1 bedroom (Queen) and 1 bathroom apartment with private entrance. This cozy Williamstown retreat will provide exactly what you would expect in the Berkshires. Walking distance to downtown Williamstown and the newly created bike path. This unit provides off street parking with plenty of privacy, and can truly transform your stay.

Historic Cozy Cabin Six

Soak up this fully renovated and modernized cabin from the 1920s. We kept and reused many vintage materials and fixtures while expanding its footprint with a new bathroom. This charming cabin has also been re-sited so that it is now in proximity to the former Inn at Oak Hill B&B which affords it shared use of amenities like parking, laundry, and privacy. Many antiques decorate the interior including a beautiful brass bed not to forget the coziest kitchenette in the world!

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

Stunning studio in the heart of Troy: Raven's Den

Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

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.

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.