Pet-friendly holiday rentals in Berkshire County

Hygge in the Berkshires. We chose this house as it is very close to Berkshire school....we found out the hosts are alumni! We loved staying here. So quiet, large enough for the teens to get their own space, but plenty of hygge. The house is on a quiet road, but it was always plowed. The stillness led to the best sleep I've had in a while. The owners are very responsive to all questions and so patient. They also provided us with some local jam and snack, so tasty. We look forward to staying here in the future. Thank you Michelle and James!

fantastic and cozy, nice backyard, well equipped with amenities as well

Staying at Amanda and Andrew’s place in Canaan, CT is an exceptional airbnb experience. The home and property are in excellent condition, exactly as pictured in the airbnb profile . And, Amanda and Andrew are quintessential hosts, friendly and responsive. We cannot recommend staying here highly enough. Thank you Amanda & Andrew !

Wonderful place to stay!! Was so lovely cooking dinner and the place is very cozy- lots of games. Great price for the amount of space. They shoveled the driveway for us twice which was so nice. Would definitely stay again.

We absolutely loved staying at MacMountain House! So lovely and comfortable and very clean. It was the perfect place for a ski weekend at Butternut and Catamount. We can’t wait to return!

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!

Nice private location, overlooking the river out back. Plenty of wildlife can easily be spotted by the patient observer. The home was very comfortable inside and out. An abundant variety of music and movies were readily available during our stay. We're looking forward to our next stay for more time in this relaxing location.

Awesome host I had a few workers staying there for the week. They had nothing but good things to say.

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.

I hope to be able to return to the Berkshire region soon, and I will definitely check availability again.

Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

Fantastic experience and stay. Justin was responsive and communicative as needed. Instructions were clear. House is exactly as described and very spacious. Excellent common spaces with THREE living rooms: this is super important for the adults and kids to have their own space. They were roomy and comfortable. TVs in good working order and hooked up to whatever you want to watch. Moreover, the bathrooms and kitchen were spotless. Everything worked. Adequate and more than sufficient lighting (for brightness or for ambiance). We never used the hot tub but it looks clean and maintained. Area is close to several ski resorts but 20-30 minutes from being busy.

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 at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

I have nothing but wonderful things to say about Teva and his lovely home. The house is spacious, tidy, comfortable, and the surroundings are beautiful and peaceful. The beds were comfortable and everything you would need is there. We skied at Catamount which was ~20 minutes away - super convenient. Finally, and most notable, the overall experience and Teva’s attention to his guests’ experience was outstanding. He promptly and proactively reached out with local recommendations, was accessible during our stay for any questions, and made us feel right at home. We hope to come back over the summer for a little getaway.

Rachel was a wonderfully responsive host. The house was exactly what I was looking for—warm, welcoming, and perfect for me and my pup. We felt instantly at home. The kitchen was amazing, and I especially loved the sound system that let me play my own music throughout the space. It was the perfect hideaway retreat, and I’m so grateful to Rachel for the opportunity to enjoy her beautiful home. The pellet and electric stoves added an extra touch of coziness, making the cottage feel even more relaxing and inviting. Highly recommend!

I was looking for a month-long stay in the Berkshires, and the barn was the perfect home away from home! It is such a uniquely charming space in a beautiful, peaceful area (even with train tracks close by, they were not very frequent). Abigail was always super responsive and helpful when I had questions and very friendly; I wish all hosts were like her! She also has the best recommendations for restaurants and things to do. Her, and the property manager, Robinson, were both quick to act if I had an issue, and they’re both so nice! I would definitely stay here again. Thank you for everything, Abigail!

Awesome place to stay very close to Jiminy Peak for a ski weekend. It was spacious and clean. The kitchen was great to cook meals. Would definitely come back.

The house was in such pristine, clean condition upon arrival with an amazing kitchen and furnishings. Bradley left us a bottle of wine as a welcoming gift along with an organized binder containing house rules, helpful tips, and several recommendations for the area. The home is a perfect size for a couple’s getaway and could easily accommodate a family. The home has several amenities that one may not expect to be included while staying at a typical Air B&B, which instantly made us feel at home and made settling in seamless. The home itself is private enough to feel secluded while secure and at peace, and is a mere minutes drive from the nearest town with everything you need and more. The hot tub was a major plus and is of the higher quality. Bradley is a proactive host who prioritizes communication to enhance guest’s comfort. I forgot a clothing article after checkout which Bradley discovered and immediately offered to mail to me. Best Air B&B experience of mine to date. 11/10

Gillian was a super host. The place was clean and ready for us when we arrived including a decorated Christmas tree, doggie dishes, and a full wood pile. She got back to us in a timely manner for all questions. And all expectations and facts about our stay were communicated in a clear way. Thank you Gillian!

We love staying on the Johnson’s property. This was our first time staying at the farmhouse and it was beautiful. They upgraded everything just enough to have new appliances and a beautiful kitchen, but kept it restored enough to have that old farmhouse feel. My children sprint to get inside to see Talitha’s welcome basket. She always does something special for them and even has a toy for our dog! As always every sq in of the house is spotless, not just the inside, but their entire property. Kyle’s always around if anything comes up and spoils my kids letting them help with the horses. He makes sure they always have special horse treats to give them. There is always plenty of wood for camp fires and S’mores kit. Looking forward to go back in the fall! The Johnson’s are the true definition of a “Super host” Thank you

Old fashioned but functional decor. Quiet, safe. Close to Jiminy peak.

This is honestly one of the best places we have stayed in. The apartment is spacious, well maintained, and well organized and stocked with everything a family needs. Clearly, Scott and Hilary have thought a lot about how to make their guests' experience as comfortable as possible. We especially like to cook (and eat), and we have never found a kitchen so well organized in a short-time rental. The drive to Jiminy Peak is only 12 minutes. Highly recommended!