Pet-friendly holiday rentals in Berkshire County

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.

Paul’s house was great! Highly refs if you’re skiing in the area.

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 !

My partner and I (and our pups) loved our stay at Mian and Anthony’s home! The home was in a perfect location for what we needed, clean and comfortable, and overall great vibe. ✨ Hosts were super friendly and helpful. We would definitely stay again next time we’re in town!

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 enjoyed our stay with our family. Great places to hang out and eat together. Also liked the quiet spots for reading.

A great spot for a getaway in the Berkshires! We stayed for a weekend when we had a wedding in the area and wanted a place where we could bring our dog. This Air b&b was perfect - private, quiet, spacious, and in a good location for walking the dog. Highly recommend if you’re looking for a place to stay in Lee/Lenox.

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!

We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

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.

This was our second stay after the first a year ago. So we knew what to expect and were not disappointed. This sweet place and location are perfect for a Berkeshire vacation combining hiking with the amenities of Great Barrington.

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!

We enjoyed our stay at Elijah’s place. It was just as described and Elijah was very responsive before and during our stay.

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

The place was spotless, beautifully decorated, and had all the amenities I needed for a comfortable visit. The host, Georgianna, was extremely responsive and accommodating, making check-in and check-out a breeze. The location was perfect—close to Jiminy Peak Mountain Resort, yet peaceful and quiet at night. The little touches, like complimentary snacks, made the stay even more enjoyable. I would absolutely stay here again and highly recommend it to anyone. Thanks for a fantastic experience!

This is a very beautiful Berkshire property that is also very conveniently located. The 2 bedroom barn is spectacular and is where we 5 spent all of our waking time. The farmhouse is where the rest of us slept (3bedrooms). We used the fully equipped kitchen in the barn. We didn’t spend our together time in the house as it isn’t as open, light, contemporary or spacious as the barn. The house does have smaller dens/living rooms to accommodate groups bigger than than the 5 of us. Both the Barn and the house have gorgeous backyard panoramic Berkshire views - one with a patio and the other with a deck. Perfect place for us (5 older women) and a perfect place for multi family and/or multigenerational clan to enjoy time together This is a great Berkshire location with lovely hosts!

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!