Kid-friendly vacation rentals in Berkshire County

A beautiful serene home set up with everything you need. We loved the space, both inside and out. There was a country store right down the road that had amazing food. Enjoyed relaxing on the deck after a great day of hiking. With so much hiking in the surrounding area, we are already looking forward to booking again.

The house was perfect! Beautiful property, lovely house, responsive hosts.

We had a wonderful stay at this peaceful and comfortable lake house. The setting was serene—perfect for a relaxing getaway—and the home itself was clean, cozy, and well-equipped. The owner was incredibly helpful and responsive, always quick to reply to any questions via text, which made the whole experience smooth and stress-free. Highly recommend!

Lovely house with all the necessities. Beds were comfortable, kitchen had all the necessary items and bathroom was clean. It was a perfect retreat and we enjoyed sitting outside around the fire pit.

We loved staying at Carolyn’s place. It was just how the listing and photos described: clean, private, had plenty of amenities, etc. Carolyn was quick to respond to questions, and graciously let us return after checkout to retrieve something we had left behind. Would highly recommend this place if you are looking to stay in the berkshires!

Great location with easy access to surrounding areas where there is always something to do! John was very responsive and we really enjoyed our stay in his home. Very comfortable and clean. Quiet neighborhood close to town. Would highly recommend!

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Really clean and spacious place. The house is in a really quiet and pretty little town near a lot of resorts. Christopher was super thoughtful and communicative. Would definitely recommend.

Fantastisch!! Charming, comfortable, quite and close in. Love this old house with beautiful woodwork, kousa dogwoods in full bloom in the yard. Great stocked kitchen, although we ate out at the many yummy cafes and restaurants. Mooncloud was a favorite! Comfy, spacious living room. Nice large dining table. Trice was a wonderful host, quick to respond and let us enjoy our space! I am so glad I took a chance on airbnb again - this was one of my favorite stays on airbnb and my favorite in Great Barrington! Would definitely book again!

Our second stay here! Had fresh coffee available for the morning and eggs in the fridge. Thank you Joy!!

Went for a Berkshire School reunion the two of us, perfect spot. Charming quiet grounds, perfect location for accessing Berkshire School, clean, Keurig, comfortable bed, amenities as stated (and quick confirmations from host), super easy process for check in and check out. Asked many questions and host responded very quickly and was very friendly in her communications.

Larry and Lana were perfect hosts. Very welcoming and helpful with local advice. There's a lovely walk around their property- just under half a mile so great to stretch early morning legs.

Wonderful place to stay for an anniversary clean rustic apartment with a welcoming feeling, it felt like a cabin 10/10 would recommend 🙂‍↕️

Lovely, comfortable place with a great location—I didn’t realize all the great places to visit near us, even within walking distance, until we arrived. What a delight to find. Loved the art and amenities in the room. Thank you for a good motel experience in GB!

This was our 2nd weeklong stay. The space is clean and bright. Heating details were clearly explained. It was quiet and peaceful but only a 7 minute drive for milk I forgot to bring for coffee. We saw a small bobcat in the front yard on our last morning. Beds were very comfortable. Hosts were friendly and responsive. I’d recommend this place to friends/family and hope to stay again.

Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

Jiminy Peak is a great family mountain. Christina's place is perfectly located to do everything right out your back door. Christina was an excellent host. Thank you.

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Ashley has a great place!! It was a fantastic place to visit with my friends and reminisce. Weirdly, this rental turns out to be the place my great grandparents lived and did business as my grandma grew up. I did not have any ghostly contact with my relatives in the apartment (I was kind of hoping and not hoping to see them 😂), but I still had such a meaningful time sitting in the spaces they did so many years ago. Ashley is an excellent host and I will come here again next time I “come home”. 😊

My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

In town for a wedding at Mass MoCa with my girlfriend. This apartment was extremely quiet, convenient, clean, cute and convenient. Highly recommend!

Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

We stayed at Renee’s place during a summer festival weekend hosted at the mountain and it was perfect for our needs! Comfy bed, good kitchen set up and a nice place for lounging in between festival events. Would definitely stay here again!