Vacation rentals in Williamstown

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Top-rated vacation rentals in Williamstown

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Guest favourite

Apartment in Williamstown

4.96 out of 5 average rating, 298 reviews

New Studio In Town, By the Water

★ 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.

Mar. 28 – Apr. 4

$270 CAD per night

Guest favourite

Home in Williamstown

4.99 out of 5 average rating, 108 reviews

The Yellow Cottage at Williamstown | Four Bedrooms

Comfortable, charming and quirky Victorian cottage. Killer location by Williams College, The Clark, MassMOCA, Williamstown Theater Festival, Spring Street and wedding venues: Cricket Creek Farms, Bloom Meadows, Williams Inn and Mass MOCA. Regional ski resorts, Mount Greylock, trails, rivers, lakes, golf, are all close for the choosing. Tucked away in the upper west corner of the beautiful Berkshires, bordering NY and VT, adventure awaits in every direction...or doesn't. You get to choose.

Feb. 17 – 24

$403 CAD per night

Superhost

Apartment in Williamstown

4.86 out of 5 average rating, 198 reviews

Williamstown Apt. on Green River Walk to Williams!

This Charming 3 bedroom apartment has hosted celebrities, published authors and world travelers. A deep sleep is guaranteed as the sounds of the Green River lull you to bed. You face the Green River when you sit on the back deck. Convenient to hikes across the street at the the Taconic Golf course, Williams College just two blocks away, The Clark Art is a 15 minute walk, and the apartment is perfect when you want to walk and explore the restaurants that offer take out in Williamstown, MA.

Dec. 2 – 9

$319 CAD per night

Guest favourite

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. 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!

Feb. 19 – 26

$263 CAD per night

Guest favourite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

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.

May 8 – 15

$129 CAD per night

Guest favourite

Home in Williamstown

4.98 out of 5 average rating, 100 reviews

Quality, Comfort, Charm in Williamstown Center

Stay at this brand new old 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.

Dec. 20 – 27

$473 CAD per night

Guest favourite

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 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.

Jul. 15 – 22

$217 CAD per night

Guest favourite

Bungalow in Williamstown

4.89 out of 5 average rating, 201 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.

Oct. 11 – 18

$383 CAD per night

Guest favourite

Cabin in Pownal

4.97 out of 5 average rating, 173 reviews

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 kitchette in the world!

May 17 – 24

$172 CAD per night

Guest favourite

Barn in Williamstown

4.97 out of 5 average rating, 261 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment in a New England home next to the Green River. Comfortable with unique furnishings and back door to river patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper tri-fold mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. Due to Coronavirus we are doing extensive disinfecting and allowing for 72 hours between bookings.

Feb. 21 – 28

$226 CAD per night

Guest favourite

Apartment in Pownal

4.94 out of 5 average rating, 179 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

Apr. 22 – 29

$167 CAD per night

Guest favourite

Apartment in Williamstown

4.93 out of 5 average rating, 234 reviews

COLD SPRING

This cozy, quaint and quiet apartment offers the perfect Berkshire county getaway. Just a drive away from Mount Greylock National Park, Jiminy Peak Mountain Resort, and the Tony-Awarded Williamstown Theatre Festival. Enjoy the mountain views, in this two bedrooms 1 bath rental with fully equipped kitchen and skylight vaulted ceiling.

Aug. 26 – Sep. 2

$271 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Williamstown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Williamstown's top sights

Mount Greylock213 locals recommend

The Clark Art Institute330 locals recommend

Williams College42 locals recommend

Stop & Shop61 locals recommend

Water Street Grill21 locals recommend

Coyote Flaco44 locals recommend

Other great vacation rentals in Williamstown

Guest favourite

Guesthouse in North Adams

4.92 out of 5 average rating, 179 reviews

"Worker's" Cottage (circa 1860).

May 15 – 22

$200 CAD per night

Guest favourite

Apartment in North Adams

4.97 out of 5 average rating, 413 reviews

Steps to MoCA, 2bd + SAUNA! Near Ski!

Nov. 12 – 19

$271 CAD per night

Superhost

Condo in North Adams

4.91 out of 5 average rating, 209 reviews

Downtown Flat Iron Condo - walk to MoCA #12

Jun. 11 – 18

$170 CAD per night

Guest favourite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Aug. 8 – 15

$153 CAD per night

Guest favourite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Sep. 27 – Oct. 4

$132 CAD per night

Guest favourite

Apartment in Stamford

4.86 out of 5 average rating, 274 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

May 13 – 20

$184 CAD per night

Guest favourite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Jul. 13 – 20

$184 CAD per night

Guest favourite

Home in Williamstown

4.81 out of 5 average rating, 170 reviews

Walking distance to downtown

May 31 – Jun. 7

$451 CAD per night

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Quick stats about vacation rentals in Williamstown

Total rentals	130 properties
Rentals with dedicated workspaces	60 properties have a dedicated workspace
Pet-friendly rentals	40 properties allow pets
Family-friendly rentals	90 properties are a good fit for families
Total number of reviews	6.4K reviews
Nightly prices starting at	$83 CAD before taxes and fees

Vacation rentals in Williamstown

Top-rated vacation rentals in Williamstown

Apartment in Williamstown

Home in Williamstown

Apartment in Williamstown

Cottage in Williamstown

Guest suite in Williamstown

Home in Williamstown

Guesthouse in Williamstown

Bungalow in Williamstown

Cabin in Pownal

Barn in Williamstown

Apartment in Pownal

Apartment in Williamstown

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Williamstown vacation rentals

Stay near Williamstown's top sights

Other great vacation rentals in Williamstown

Guesthouse in North Adams

Apartment in North Adams

Condo in North Adams

Apartment in Bennington

Guest suite in Hancock

Apartment in Stamford

Apartment in Bennington

Home in Williamstown

Quick stats about vacation rentals in Williamstown

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore