Kid-friendly vacation rentals in Great Barrington

We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

Michelle was incredibly gracious and responsive when we called late after our check in with a question about the heater. The place is gorgeous and you can tell that she pays attention to every detail and is doing all she can to make it a pleasant stay. The decor is perfect, the amenities are perfect. We had plenty of room to cook and host a dinner with four adults and two kids. We lit a fire, played games and relaxed. The bedding is so comfortable and we all slept so well.

Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

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!

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.

The house was decorated so nicely. It felt like we were on vacation even though we were staying just for the night. Everything was super clean especially the two bathrooms. The host had a lot of amenities like snacks a bottle of wine, coffee tea it was great. We would stay there again

From the neighboring farms to the stunning sun and moon sets to the safely fenced in yard and warm inviting space -Austin’s place in Hudson is a treasure. Hearing the horses whinny and seeing the cows at the fence was a dreamy country experience. Austin was beyond helpful from before I arrived as well as during my stay - he has earned the title of Super Host! Going into Warren St was amazing. Le Perch, Savonnas Trattoria and Bobba Louis were a great way to fuel up after shopping in the cultured eclectic variety of shops in the area. I would return in a heartbeat and felt melancholy while packing because I honestly wished I had booked for more than one week.

Tommy was a very respectful and responsive host. The house is beautiful, with plenty of space to hold a medium sized group. Large kitchen/dining room, and comfortable living room for group dinners and game nights. Close to a variety of towns providing flexibility to explore.

Rachel was super quick to respond which was very helpful for me when last minute planning. In addition, I was traveling solo with my dog and she (and her super seeet dog)was sooooo nice to hang out with him when I had to go to my jobsite. The bedrooms are all super cozy, it was hard to pick one for the two nights I was there solo. The bed was very comfortable and a great night sleep away from home is hard to find. Love the natural light and the plants throughout. Made me feel right at home. Would stay again next time I’m in town for work!

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 :)

Perfect spot right in the downtown area of Albany. Super walkable area, space was as depicted and photos matched the listing. Very responsive hosts and extremely accommodating! Would recommend 😊

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!

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!

The place was as described by the host. Perfect location.

Great place to stay. The hosts are great and very communicative. Close to a bunch of food spots as well!

The place was wonderful. Very charming and homey, spotless with all the amenities and conveniences you could need. The information included in Joe’s binder gave great recommendations for meals and attractions within easy driving distance. We had never traveled to that area before and found the local scenery beautiful. Thanks for a lovely experience!

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

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”. 😊

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

A friend and I stayed for the weekend and it was perfect! The location is walkable, with restaurants in walking distance. The condo was comfortable, super comfy and homey. David provides all amenities and is super helpful. He provides some of his own recommendations and is super responsive. We definitely would love to stay again.

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

Had a great stay at Jo-Anne’s for a wedding as MASS MoCA. Space was clean and cozy. Bed and pillows were comfy. Very walkable to places around town. The cars driving by were a little loud for a light sleeper, but with some earplugs it was fine. Jo-Anne was very helpful and responsive.