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 & Sarah’s cabin was stunning. It was just as pictured, warm and inviting. There were lots of wonderful details throughout the space; it was very well curated for a relaxing weekend with family. Definitely more amenities than the average AirBnB, we felt right at home! We would definitely book again!

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.

Beautiful space to cozy up and enjoy peace. I needed a mental health getaway to enjoy nature and respite from the day-to-day. The wood-burning stove was incredible, already set up with everything I needed, ready to have a fire. The fully functioning and easy-to-use kitchen was great, and there were beautiful paintings everywhere. Be mindful if you have a dog—I did see a bear down the street about a mile away, which is expected in Western Massachusetts, so keep pets leashed. As described, the house connects to an apartment on the other side, with a door leading to their porch through one bedroom, and a window in the other. Vintage cabin vibes inside. Beautiful views no matter which way you look. An enormous and diverse selection of books, old and new. I stayed one night and wish I could stay another. My lab enjoyed relaxing by the fire’s warmth. Easy to find and a short drive to nearby towns.

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 !

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!

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!

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.

We stayed for a weekend and we felt right at home! Any issues we saw was handled promptly and the host was nice. The place itself felt cozy and inviting, perfect for what we were looking for - a peaceful retreat after work and spend time with family and friends. The furniture was amazing as well, and we loved the mattresses! All of the beds felt comfortable, and the comforter was light, but the same time warm. As far as things to do, we played ping pong, nba jam arcade and some card games which made time pass by quickly. The hot tub was also nice, easily fitting 7 people. The town of barrington is around 20 minutes away, so you can also explore the area if you so choose. Overall, I recommend this place for people looking for a break from the hustle and bustle of city life. Looking to see if we can go again on a warmer time so that we can use the pool next time.

We had a very nice stay here. The place was clean & pleasant. would definitely come back.

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 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.