Pet-friendly vacation rentals in Berkshire County

We had a wonderful visit to Alissa’s cabin! It was just what we needed while visiting friends in the area for the holiday. Quiet, comfortable, and plenty of room to explore outside. Would love to stay here again on our next visit!

AMAZING! Some friends and I escaped the city for 3 days and stayed at this cabin. We will definitely be returning. The place was huge and so cute. Joy was more than accommodating. The hot tub was huge and clean. The wood burning fire places were so cute. Overall amazing place to say I would 1000% recommend.

We had a great stay at Michael’s cabin. His communication was thorough and he was very responsive to any questions we had. The space is comfortable and peaceful. Just a heads up- a lot of the windows don’t have curtains (upstairs bedroom and bathrooms). I imagine the only things that would see you are deer, but the sun definitely woke us up in the morning :) Well stocked kitchen, which was a huge plus! Thanks for sharing your great space with us!

Matt and Sarah's home was beautiful and peaceful, and they were both incredibly responsive and helpful leading up to the stay and throughout the stay as well! 10/10 would recommend staying here!

Kate was so responsive and kind and made us feel very welcome. The house is full of charm and so cozy. We spent our vacation spread out on comfy couches around the big woodstove. The area is beautiful and peaceful, I loved taking my dog for walks down the road and letting him run around the woods in the backyard. Everything was clear and well communicated and we felt right at home. Thank you Kate!

Had an amazing stay! This cabin was absolutely perfect for a weekend getaway. The location is so peaceful and quiet, making it the ideal spot to relax, but still close enough—just 20 minutes!—to great shopping and restaurants when you want to explore. Highly recommend!

We came to Otis with our 3 young children with the plan for them to learn to ski at the nearby ski school/mountain. We had a wonderful time and John and Loren’s house was perfect for us. They are lovely, accessible and accommodating hosts! We had the good luck of a snowy weekend and the cabin and property were just gorgeous. The cabin is simple, but very comfortable and we enjoyed how cozy it felt. Our kids slept well and and had so much fun, so did we!

Katie's house is warm and comfortable with a great wood stove/fireplace and a well equiped kitchen. You can walk out the door and into the lovely woods. Our three generation family of seven was very comfortable. We would love to return.

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!

The house was a happy place to spend holidays with family. Our two-year-old loved the play kitchen next to the real kitchen and we loved the great room with the gas fire place. The house was tastefully and lightly decorated for Christmas, which we appreciated coming from afar, and there were enough pots and pans to, as the host said, prepare a feast. We wished we had known the basement was not heated, though perhaps we missed that, but we made use of that fun space anyway with the help of warm sweaters. We would rent again!

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 !

Really cozy place. Older building, but we like that. Clean and comfortable. Didn’t realize we had access to the hot tub/jacuzzi and after a day of skiing it was so nice! My son’s girlfriend said it was one of her best days ever. The host warned us that the kitchen had minimal supplies, so I’m glad we brought our own coffee and sugar. There is a county store right across the street if you need anything. Fenced dog park nearby, unfortunately it was empty but at least the dog could stretch his legs. WiFi worked great.

Cozy home, with a very nice kitchen / dining room to gather in. High ceiling, warm lighting, and a few thoughtful antiques/decorations. Great place for evening games after a day on the slopes!

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!

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.

Great house for a great weekend getaway!

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.