Kid-friendly holiday rentals in Stockbridge

We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.

We had a wonderful stay! Our family really enjoyed this beautiful home. The house decor/art work was fantastic, the home was warm, welcoming and very spacious. There was plenty of room to spread out and everything was very clean. The outdoor space was beautifully done and was perfect for hanging out/grilling. Would highly recommend!

Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.

One of the cleanest Airbnbs I've stayed at. The place was immaculate, and had everything needed to make our stay great (coffee, tea, kitchen essentials, etc). John was super responsive and proactive, and the location was great. My only regret is that the weather didnt cooperate to fully enjoy the fantastic patio set. Would book again without hesitation.

This was a great cute quiet place that fit our family perfectly. The gaming area was perfect and entertaining. My youngest daughter absolutely loved the piano! The host was very responsive and accommodating for sure. We would highly recommend 🥰

Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Excellent stay at this beautiful house! The views were spectacular and everything was as described in the listing.

We had a great stay -- everything was very easy and Chris made sure we had everything we needed! We'd definitely stay here again!

Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

This place is a gem! The apartment has 2 private entrances, plus a parking spot that is visible from the apartment above. It is conveniently located near major stores, restaurants, and an EV charging station. My daughter and I stayed for 2 nights because we were attending a wedding in Tanglewood, just a few minutes away! The apartment was spotless, well stocked with linens, bathrobes, paper products, Keurig coffee pods, and the refrigerator even had chilled beverages! The kitchen is equipped with modern appliances and everything needed to prepare meals. There is even a stackable washer/dryer with laundry pods. The 2 bedrooms are far away from each other to afford privacy. The beds are extremely comfortable with high-quality sheets and comforters, plus extra pillows and blankets in drawers and closets. Our Superhosts, Richard and Kathleen, were extremely responsive to our needs and provided great recommendations for nearby restaurants and stores. Our stay was 100% PERFECT!

Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.

Just perfect: cozy, inviting, private. Everything you need, with lots of personal touches. We had a wonderful time!

We booked last minute to stay for a night to attend an event nearby. While our stay was brief, it was super clean, comfortable, and just what we needed. Everything smelled fresh, and Kelly’s recommendations were helpful too.

Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

It’s been a little over a week since we stayed here and I cannot stop thinking about it. The pictures in this listing are beautiful but the space is even more incredible in person. I also spent a lot of time sitting on the deck and taking in the view of the mountains - so peaceful! The attention to detail here is unmatched. From check in to checkout, everything is very clear. Communication was great. The guidebook is thorough. And, again, the space really is so well done. You can enjoy the beautiful surroundings even indoors. Highly recommend!

My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

This was our 2nd stay at Rhonda's place- felt like home again. As before, she was very helpful, thought of everything ahead of time, and was very quick to respond to all our questions. The flat is clean, cozy, and comfortable- hope to stay again sometime.

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!

Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

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

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.

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

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.