Kid-friendly vacation rentals in Great Barrington

Highly recommend Sarah’s house. We stayed in the spring and it was beautiful. Spacious outdoor area with lots to do. There was plenty of space, lots of activities and stuff for our kids to play with; super family friendly. Also very close to all the towns we wanted to visiting and natural attractions up in Hudson River valley. We would stay again thank you !

We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!

Lola's place was clean, quiet, comfy and well situated for our needs. The house is well equipped, including butter, milk and eggs in the refrigerator (nice touch). Lola is very responsive, answering any question we had in a timely manner. We would definitely recommend and stay here again.

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

Our hosts were very easy to work with. I felt they cared about our visit and wanted to accommodate us in any way that would make her stay even more pleasurable. The house offered every convenience, including kitchen items for make-at-home meals. Thanks so much, Brandon and Brian!

My daughter and I spent a lovely weekend at Chelsey and Dominic’s house. It was the perfect place for reading, laughing and lots of conversation. Easy to get almost anywhere in Hudson Valley. We enjoyed walks around the property and seeing quite a lot of wildlife. The setting is truly magical.

Great spot to gather with friends. So close to trails and lovely towns. Loved the wood stove and hot tub!

We had an absolutely lovely stay at John and Kelly's mountain retreat. Everything we could have wanted or needed -- coffee, linens, towels, etc -- was there for us. It was so tastefully appointed and just a joy to spend time there. And the views! Wow! We hope to come back here soon. Thanks for being exceptional hosts. Five stars all around!

Beautiful, clean home just a few minutes away from the centers of Lenox or Lee in either direction! We had a great time relaxing and enjoying the food nearby :)

This was a great place and Ben was super responsive. I would definitely recommend this spot!

My family and I loved staying at Tj’s place in Hudson. The apartment was beautiful and exactly as described. Four of us stayed there for a week and we were very comfortable. Tj was very responsive when we had questions or issues (which we didn’t have many of since instructions were super clear). I also enjoyed the multiple yoga classes and spa sessions I participated in at their spa downstairs. The instructors and providers were all super friendly! The town of Hudson is incredible for anyone who loves to shop, look at art, and eat good food. It’s small, but there’s so much to see and eat! Everyone in town was genuinely friendly and welcoming. This was exactly what my family and I were hoping for for our vacation. We’re grateful we found Tj’s place!

Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

My daughter and I were seeking a basecamp to explore nearby colleges but also had one day where we needed to connect to our computers for work. We slept well, had peaceful morning walks in the neighborhood, took advantage of the sunshine on the lovely deck, and enjoyed making meals in the kitchen that had more than all the essentials.

My daughter and I had plenty of space to spread out. John’s place is very comfortable, clean, and charming. Thoughtful touches like extra hooks, suitcase stand, and bench at the entry to take off our wet shoes after a rainy Spring day in Hudson. Easy walk to great coffee shop and restaurants. Would definitely return!

it was a great place to stay if you love being out and about exploring restaurants and food. the room and bed was decently comfortable. the kitchen was nice and updated as well if you want to use it. The bathroom was nice and enjoyed the shower heads. I enjoyed the cleaning service taking care of everything with very minimal instructions. very nice little place but doesn't have a lot of natural lighting since it is a basement apartment, can feel stuffy at times. It can get cold down there and there is only one heater by the bed heating the place. only complaints was how slow the wifi was and I think it's just a little dusty down there in certain parts, not sure it was worth the full price we paid but it worked for one night.

This was our second stay and would certainly return again. Love the openness of the living area, the great bathroom and the kitchen amenities. Quiet location, was perfect for our activities in Northampton.

Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!

Spacious condo, great for a weekend or long term stay

Luiza was a wonderful host. She provided detailed check in and out instructions, as well as local recommendations for our stay. Her place was exactly as pictured and cleaned wonderfully for our arrival. We hope to be back for another ski trip!

We had a wonderful stay at this beautiful Airbnb. It was comfortable clean and had all the comforts of Home Muna was a wonderful host. Very accommodating and efficient. if I had to stay in this area again, I would certainly look to stay here

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Great people great location I would definitely recommend others and a great price

My boyfriend and I really enjoyed staying at Lubov’s place it was super clean and had lot of amenities. We went around Woodstock for dinner, which is a beautiful neighborhood and not to far, great for a spot to eat or just walk around and spend the afternoon. We also visited the Kaaterskills falls which was super close so that was a wonderful bonus. Didn’t get the chance to this time but we passed many hiking trails and mountains that are in very close distance to the Airbnb! Definitely would recommend staying here to anyone who is looking for a peaceful and tranquil getaway! We had a wonderful time, Lubov couldn’t have been any more amazing! Definitely will be back soon!!

Cozy apartment, walking distance from the water front. Had a great weekend getaway.