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Family-friendly holiday rentals in Williamstown

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Williamstown

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Guest favourite

Rental unit in Pownal

4.94 out of 5 average rating, 114 reviews

"The Parlors"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile system and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

Guest favourite

Home in North Adams

4.97 out of 5 average rating, 156 reviews

Bernie's & Betty's

Comfortably sleeping 6 with a large yard, screened in porch, and newly renovated bathroom, this charming 3-bedroom house is perfect for families looking for fun and adventure in the beautiful Berkshires. Minutes from Mass MoCA, Williamstown (including the Clark Art Institute), 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.

Guest favourite

Guest house in Williamstown

4.93 out of 5 average rating, 237 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage 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

Rental unit in Plainfield

4.97 out of 5 average rating, 258 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Guest favourite

Bungalow in Williamstown

4.89 out of 5 average rating, 211 reviews

Hollywood Bungalow in the Berkshires

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.

Guest favourite

Rental unit in North Adams

4.98 out of 5 average rating, 190 reviews

Overlooking the city in a quiet 7 unit building.

This is a quiet, 7 unit, newly renovated condominium building. We welcome quiet guests who will appreciate a relaxing stay and be conscious of others around them. We are within walking distance to the countries largest contemporary art museum. The 2nd floor is an open plan divided by the stair case. Each side has a queen bed, its own closet. The full bathroom is shared with the two beds. This is a loft, there are no full walls between the two sides of the loft.

Guest favourite

Farm stay in New Ashford

4.89 out of 5 average rating, 238 reviews

Sheep Barn on the Greylock Valley Estate

Located 10 minutes from Williamstown, the Sheep Barn is a completely renovated antique barn, with 3 bedrooms, 2 full baths, and full kitchen. It's the perfect place for spring and summer getaways, cozy fall weekends, and winter ski vacations. Offering hiking trails and complete privacy, it is still close to Williams College, Jiminy Peak, and other Northern Berkshire attractions. During winter months we recommend that guests have All Wheel Drive vehicles.

Rental unit in North Adams

4.84 out of 5 average rating, 303 reviews

Berkshire Hideaway

We are walking distance from the MASS MoCA campus and a cozy place to recover from all the amazing art and culture. Hiking, beautiful views and ever changing galleries are all easily accessible. There is a permitted parking lot conveniently close by that is 10.00 for 3 nights. We can get all your vehicle info and have that ready for you. Alternatively, there is a free parking lot a couple of blocks away and on street parking in the summer.

Guest favourite

Barn in Williamstown

4.97 out of 5 average rating, 287 reviews

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.

Guest favourite

Rental unit in Bennington

4.93 out of 5 average rating, 612 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Holiday rentals for every style

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Popular amenities for Williamstown family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Cabin in Becket

5 out of 5 average rating, 265 reviews

Waldtreff - quiet grand cabin

Guest favourite

Home in Craryville

4.98 out of 5 average rating, 203 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

Guest favourite

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Guest favourite

Cottage in Shaftsbury

4.98 out of 5 average rating, 636 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Home in Northampton

4.88 out of 5 average rating, 605 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

Guest favourite

Home in Chester

4.96 out of 5 average rating, 335 reviews

Riverfront Getaway

Guest favourite

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Guest favourite

Home in Craryville

4.92 out of 5 average rating, 229 reviews

The City Farmers Upstate. Farm house with hot tub

Family- and pet-friendly home rentals

Guest favourite

Cottage in Claverack

4.98 out of 5 average rating, 259 reviews

‘Clavashack’ Country Cottage

Guest favourite

Loft in Wilmington

4.93 out of 5 average rating, 187 reviews

Walk to Village/Lake Whitingham

Cabin in Woodford

4.84 out of 5 average rating, 360 reviews

400+ Airbnb Visits: Incredible Mountain Cabin

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 514 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Guest favourite

Rental unit in Newfane

4.97 out of 5 average rating, 431 reviews

Rock River Retreat: VT Oasis Pet Friendly

Guest favourite

Home in Cheshire

4.85 out of 5 average rating, 210 reviews

19th c. Barn in The Berkshires

Guest favourite

Rental unit in Montague

4.93 out of 5 average rating, 424 reviews

Beautifully renovated three bedroom

Guest favourite

Rental unit in Northampton

4.99 out of 5 average rating, 761 reviews

North Street Nest, sunny downtown apartment

Family-friendly home rentals with a pool

Guest favourite

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

Guest favourite

Townhouse in Dover

4.96 out of 5 average rating, 143 reviews

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Guest favourite

Rental unit in Northampton

4.98 out of 5 average rating, 283 reviews

Sunny Inspirit Apartment in best downtown location

Guest favourite

Apartment in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Guest favourite

Bungalow in Easthampton

4.92 out of 5 average rating, 472 reviews

The Creation Station

Guest favourite

Home in Saratoga Springs

4.86 out of 5 average rating, 110 reviews

Saratoga Springs convenient tranquil location.

Guest favourite

Home in Ghent

4.88 out of 5 average rating, 299 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Guest favourite

Apartment in Hancock

4.84 out of 5 average rating, 141 reviews

Cozy Condo @ Jiminy Peak

Quick stats about holiday rentals that are family-friendly in Williamstown

Total rentals
80 properties
Nightly prices starting at
₹5,891 before taxes and fees
Total number of reviews
4.1T reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi

Destinations to explore