Vacation rentals in Williamstown

4.89 out of 5 average rating, 188 reviews

Cottage in Williamstown

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 .More than one dog 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!

4.99 out of 5 average rating, 115 reviews

Cottage in Williamstown

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!

Guest suite in Williamstown

4.96 out of 5 average rating, 237 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.

4.99 out of 5 average rating, 136 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.

Guesthouse in Williamstown

4.93 out of 5 average rating, 239 reviews

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.

4.98 out of 5 average rating, 105 reviews

Cottage in Williamstown

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!

Apartment in Williamstown

5 out of 5 average rating, 128 reviews

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.

4.97 out of 5 average rating, 300 reviews

Barn in Williamstown

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.

Apartment in Williamstown

4.94 out of 5 average rating, 303 reviews

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.

Superhost

Guesthouse in Pownal

4.84 out of 5 average rating, 539 reviews

Bauhaus Guest House in So. VT.

Enter through a flowering courtyard into this one room studio style guest house with full bath, closet and sliding glass doors looking out upon a lush green landscape in Southern Vermont. Parking, wi-fi and local insight included. Hosts = AMAZING :) 5 miles to Williamstown Theater Festival, Williamstown, MA 9 miles to Mass MoCA, North Adams, MA 9 miles to Bennington, VT

4.97 out of 5 average rating, 555 reviews

Apartment in North Adams

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Guesthouse in Williamstown

4.96 out of 5 average rating, 183 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Williamstown vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Williamstown

Superhost

4.75 out of 5 average rating, 98 reviews

Three bedroom two bath ranch house

AkashRating, 5 stars9 months ago

Nice house in a beautiful quiet location that’s nonetheless close to everything. We had easy access to Williams College but it’s also very close to North Adams and its museums. Doris’s communication was great and she was flexible and easy to work with. Great stay overall

4.96 out of 5 average rating, 26 reviews

Cozy Log Cottage in Berkshires on 1.6 Acres!

HeatherRating, 5 stars4 weeks ago

The cottage is absolutely charming! We loved Maggie’s thoughtful attention to detail and the cozy Ralph Lauren-inspired vibe - it truly felt like a home away from home. Maggie was incredibly responsive and helpful when we reached out, which we really appreciated. Overall, we’d happily recommend this cottage to anyone looking for a relaxing and stylish getaway!!

4.97 out of 5 average rating, 35 reviews

New Berkshire home - 3 bed, 2.5 bath w/views

AngelinaRating, 5 stars2 months ago

Trina’s place was so wonderful. The location was perfect. Just a few minutes to the ski resort which was amazing. The surroundings were so beautiful to wake up to! The pool table was a big hit with my group we had so much fun. Just keep a look out when arriving or you might miss the driveway.

4.93 out of 5 average rating, 30 reviews

Loft in Williamstown

Vacation Rental Home in the Berkshires!

MorganRating, 5 stars1 week ago

Incredibly clean and affordable home to stay. Our host was very responsive and supportive with any questions we had. I would highly recommend this home for anyone looking to visit Westfield.

4.89 out of 5 average rating, 28 reviews

Condo in North Adams

Downtown Condo - walk to MoCA

RuthRating, 5 stars1 week ago

My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

Apartment in Williamstown

5 out of 5 average rating, 20 reviews

Downtown Jewel | Stylish | Fully Stocked | Firepit

JenniferRating, 5 stars1 month ago

A most comfortable and charming stay in Williamstown within one block of the beautiful Taconic Golf course and several restaurants. Beautifully appointed - everything new and in excellent condition! Dalit is an excellent host, always responsive and resourceful. Look forward to staying here again !

5 out of 5 average rating, 9 reviews

Apartment in North Adams

Home in Mt. Greylock

MichaelRating, 5 stars5 months ago

Roberto’s place is excellent. It’s a very clean space, the bed is comfortable (and the shower pressure is great, which is always a plus). The house is spacious and filled with everything you need. It was cozy and warm for our winter stay and everything is even nicer in person than in the photos. And the location is beautiful, too. Roberto was a wonderful host — he left clear instructions for self-check-in, tips for things to see and do, and some snacks for our arrival.