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, 238 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, 106 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, 129 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.

4.98 out of 5 average rating, 425 reviews

Home in North Adams

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate. 10 min drive to Williams College & Clark. Steps to downtown & restaurants. Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

4.97 out of 5 average rating, 301 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, 304 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.

4.84 out of 5 average rating, 539 reviews

Guesthouse in Pownal

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

4.94 out of 5 average rating, 198 reviews

Apartment in Pownal

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).

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Popular amenities for Williamstown vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Williamstown

Superhost

4.74 out of 5 average rating, 99 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, 27 reviews

Cozy Log Cottage in Berkshires on 1.6 Acres!

BrianRating, 5 stars4 weeks ago

I would recommend this cabin to everyone! Beautiful place and great host !!

Superhost

5 out of 5 average rating, 3 reviews

Modern New Home -Walk to Campus, Williamstown 183

TaylorRating, 5 stars1 week ago

If you are looking for a clean, pristine and welcoming home this house fits the bill perfectly. The house and all its interior fixtures/appliances/bathrooms/etc seemed brand new and spotless and inviting. Clearly these owners understand the value of a thoroughly clean and welcoming vibe upon entering the house for the first time. It felt like a high end boutique resort home. The owners/hosts were super responsive and gracious with every request we had. Williamstown is a beautiful spot and we would highly recommend this home if you’re thinking of going there to visit.

4.98 out of 5 average rating, 41 reviews

Cottage in Pownal

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

HedyRating, 5 starstoday

outstanding! we stayed for over a week to be close to Williamstown, which was only a 10 minute drive as promised. Beautiful quiet setting, quick responses to any questions, and a well-appointed cottage with all the necessary amenities. hope to stay here in future.

4.89 out of 5 average rating, 28 reviews

Condo in North Adams

Downtown Condo - walk to MoCA

RuthRating, 5 stars2 weeks 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.

4.91 out of 5 average rating, 35 reviews

Home in Pownal

Modern Farmhouse Retreat

AlexRating, 5 stars2 weeks ago

Unfortunately we could only spend two nights here. We loved the spaciousness of the downstairs. It was great to be able to walk our dog nearby. Williamstown and Bennington are very close. I loved hearing the rain on the roof the first night. The birds were amazing. We loved our experience here!