Pet-friendly holiday rentals in Williamstown

Had a great time with friends for the weekend. Beautiful view of the lake and plenty of space. Everything is labeled in the kitchen so you can easily find everything you need!

Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!

We stayed for a weekend at Kelley and Jason’s home in Vermont and everything went great. From check in, to the local recommendations, to the quiet setting, we enjoyed a great time away. Hot tub, game room and the large deck were great.

We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

Our stay was short, but had a good one. The home is comfortable and spacious. Great for families, just be mindful that master suite is in basement with steep, cramped stairs for anyone with mobility issues. Other than that the place is as pictured, beds and pillows were comfortable and clean. We didn't have a chance to use it but sunroom and back yard looked lovely.

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

Loved our stay ... We had a nice family dinner , could sit out on deck and enjoy the gorgeous view and our meal and then were able to take a short hike up the back trails and enjoy the gardens and store .... Hannah was awesome and very responsive and checking in to make sure that we were all set .. Thank you so much for allowing us to stay and enjoy our stay. We had a perfect weekend. Thank you, Garry and Family

Absolutely stunning property with incredible resources surrounding - trails on the property, trout pond to swim in, warm showers, peaceful energy. Highly recommend!

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Robert was an excellent host. Proactively reached out with help to find the home, and a whole host of recommendations. Great space, very private, and had everything you could need.

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Very clean. Well furnished kitchen. Spacious. Good value.

This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!

Lenore's place was very cozy. We felt right at home. We added guests (including a dog) after initially making our reservation and it was no problem with the host. Just a note, it costs a fee to add more guests on Airbnb. Overall our stay was lovely and our hosts were very nice, responsive, and welcoming. 10/10, would recommend.

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

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!!

This was a perfect place for our family to stay while visiting Williams College. Good location, comfortable home, and great suggestions for taking advantage of time in the Berkshires. I would stay again if our family ends up having students at Williams!

Great location and a really homey, spacious, and beautiful interior. And the host made check in and check out super simple. Great experience. Would stay again!

Loved our stay! Very clean and quiet. Nice and private as well. They allow pets which is awesome. Would love to stay here again.

This cottage was Magical. Reminds me of a cottage out of a storybook. Incredibly peaceful and quiet tucked in the woods. The cottage itself was so lovely and Lisa thought of everything. Well stocked with kitchen, bathroom supplies. I loved the games and record player with tons of records. The cottage is super clean and Lisa was an incredible host. I needed to contact her and she was very responsive and thoughtful. I would highly recommend and will be back in the fall ✌🏻

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!

Katie's place was great--very stylish, conveniently located, and well maintained/cleaned. Loved the renovation of the older building to create a contemporary space while incorporating some of the historic beams and brick work into the design. The living area and kitchen were spacious, comfortable, and well-appointed. The beds were very comfortable. It was great to have a dedicated parking space. The street is busy and well lit, so we were happy to have ear plugs and eye shades when trying to sleep. The location is convenient to MassMOCA and some great restaurants. All in all, a fantastic stay!