Pet-friendly vacation rentals in Berkshire County

What a beautiful experience it was staying Lissette’s Airbnb, the house was gorgeous, the views were breathtaking, and she was so responsive to questions we had!

We traveled with a small group from Chicago to Austerlitz for a wedding and had a beautiful peaceful weekend out in the country. Joy and Jason left great instructions for us to feel completely at home and comfortable. The house and grounds were just beautiful and clean. Their place is perfect for a break from the city where we could wake up to the birds and beautiful light.

Actually I don’t write many reviews, but Michael’s cabin definately deserves one. The cabin is beautifully located and decorated and really gives you a homy feeling. Michael also went the extra mile to make us feel comfortable. It was the perfect place for a weekend retreat!

Timothy was a responsive, helpful host, and his property was beautiful. My friends and I had a wonderful stay at his peaceful home. The surroundings were beautiful, the house was clean, comfortable, and well equipped - a great place to relax and hang with friends.

We loved our stay @ Matt’s place. Everything was absolutely perfect - they had everything we needed and more. We are already wanting to plan a trip back. I could not recommend staying here more. This was the best air bnb anyone at our group had ever stayed at.

Communication was seamless! Kate was responsive, ensuring our stay was comfortable from start to finish. The instructions on how to take care of the cabin are excellent. The woodburning stove is a delightful touch.

We booked Denise’s place for a weekend getaway from NYC. It was quiet, comfy, romantic, and relaxing. We really enjoyed the fireplace and the nice porch for stargazing. The master bedroom was huge and a great place to relax and enjoy sleeping in. We went apple picking at the orchard across the street and had a great time. There are also several restaurants within a 15-20 minute drive that have great food and intimate settings. I highly recommend this as a relaxing and quiet getaway.

The Cabin is beautiful, has everything you'll need, and is located in such a huge remote area within few minutes walking distance from 2 very nice lakes. We had real fun!

Lovely setting, abundant room in the home, excellent responsiveness from host. Michelle and James were very welcoming.

Loved staying at Maureen's cottage for peak leaf peepin' season with my dog! The perfect way to kick off the fall season in the Berkshires. The cottage is right on a small lake off a quiet county road, so it's very secluded and peaceful. At the same time, Maureen's place is located so close to a ton of Berkshires attractions like the Norman Rockwell Museum, Stockbridge, Great Barrington, Edith Wharton's home, tons of beautiful state parks and hiking trails. Most fun things to do are within a 15-20 min drive. The cottage itself was delightful to return to, with a ton of kitchen amenities, which made retiring to it in the evening very enjoyable. The cottage was extremely dog friendly, with easy to clean carpets and rugs everywhere—my dog also loved lounging outside in the back seating area to enjoy the fall breeze. Comfortable bed, clean bathroom. Maureen was also extremely responsive to my questions about trash and once when I accidentally locked myself out! Thank you for a great stay.

This is our third time at Amanda’s beautiful home and we’re already looking forward to our next. The peaceful fields, birds, wetlands, and quiet all around are sublime. The house is great for cooking, hanging out, and just staring out the windows. Very comfortable, well appointed, and classy. Much appreciated!

Very spacious home, perfect for my intergenerational family of six, from toddler to grandparents, and pet friendly for our dog. Comfortable beds, lots of pillows and towels, great hot water in the shower. Friendly and responsive host. Easy walk into the lovely town of Great Barrington and short drives to other places in the area.

We had a really nice stay in this lovely house. Our experience was more consistent with most reviews - it's nicely furnished, has everything you need, feels peaceful and secluded in the woods, and my kids went wild over the zipline and trampoline. I did not have the feeling that the recent reviewer did who said it felt too lived in - it was not one of those places where there is zero evidence that it's someone else's house, but neither did it feel like we were walking into their lives. The hosts were incredibly nice and very responsive. And the location is so great - so many incredible hikes. We randomly chose Stevens Glen since we hadn't been before and it was close, and it was gorgeous.

Britta’s accommodations for a 10-person group of friends was perfect! Everyone was able to have their own space and the kitchen was spacious enough for us all to enjoy everyone’s company and be able to cook with ease! The little “welcome” gift of goodies was an additional treat!

This place was perfect , we rented it for our wedding last weekend at Greywacke Meadows for two nights. It was awesome to have such a cute place to get ready in with my bridal party. Everything was clean and exactly like the pictures. We had a great time , highly recommend!

Perfect house for hosting family Thanksgiving. Well equipped kitchen. Enjoyed the fireplace. Very cozy and comfortable. A guest book should be included too! We did enjoy outside, even the snow. Summertime at this house would be great.

We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

Staying at Anna's place, a beautiful 3- story Airbnb in Lanesborough, MA, was fantastic (3 couples and a 1- and 10-year-old). The place was easy to find and very clean. The property was beautiful and exactly as described. The house is impressively stocked with everything you might need. The layout is beautifully designed, making it a breeze to navigate and relax. There were lots of toys for the kids to play with and don’t forget about the TV room which was awesome for gaming and/or watching a movie. The centralized kitchen and family room were great for us all to gather in. The cherry on top is the fantastic jacuzzi—perfect for unwinding after a day of exploring the area. We look forward to returning in the future and highly recommend it!

What a great stay! We did a quick overnight here and the place is spacious and impeccably outfitted. This is now on our list of favorites!

The house is charming but the beautiful collection of both vintage and antique pieces make it an exciting and warm home. It's fun just to walk around and look at all the pieces in the nooks and crannies. Most importantly it is warm and welcoming and was the perfect place to gather our family for my son's wedding weekend. The beautiful kitchen with it's rambling island was the anchor for many meals and conversations especially the late snack after returning from the wedding. The view of the lake from the dining room early in the morning was breaktaking. I can't say enough about the house! I was sad to leave it!! It's just a very special place! Meredith and Jason were very responsive to offer inquiries and flexible to our requests. They were perfect hosts!

A wonderful experience - house was well laid out with enough privacy for remote work and gathering spaces to socialize. Furnishings were comfortable and had everything you needed. grounds were quiet peaceful and pristine. Will return in the future for sure! Close to north adams Mass Moca for an outing.

Kelsey’s place was nothing short of perfect. My family and I hadn’t been back to Mass in many years, and we needed a good place to have everyone together again in one place - this place fit the bill and more! The house and backyard are beautiful. You get plenty of space while still feeling cozy. The backyard was perfect for a BBQ and the grass area provided plenty of space for my kiddo to run around and play. You’re also wicked close to the lake and have plenty of places to explore. Kelsey was extremely responsive and kind, and even let us extend our stay a few days because we were having such a wonderful time. I hope to stay here again when we come back next year!

We had the pleasure of staying at Min Ji's Airbnb over Thanksgiving, and it was a fantastic experience! We were two families with kids, and the house provided plenty of space for everyone. Each family had their own private area upstairs with 2 rooms and a bathroom for each family, and downstairs felt spacious enough to have a more lively area for the kids in the living room/sunroom and a quieter area in the library for those who wanted to unwind. The sunroom was a perfect playroom for the kids, it was nice and sunny during the day with beautiful view on the surrounding nature. They had a little picnic table where they could draw/ do arts and crafts and a play kitchen which was a hit with the little ones. The living room had a nice gas fireplace which made it very cozy. Bedrooms and bathrooms were very comfortable. The kitchen was well-equipped, making it easy to prepare our Thanksgiving dinner. The entire house was well heated, even the sunroom which could have been cold in the winter.

We had a great stay! Jackson was available at arrival and even helped us carry our things inside. We fully enjoyed the screening room and the plethora of movies available to us!!!! The bungalow was perfect for both our quiet Thanksgiving dinner for two and our mini birthday celebration with grandchildren the next day. Our host was responsive to all questions/requests and checked in a couple times to make sure we had everything we needed. We will likely stay again when we visit the Berkshires for family events!