Family-friendly vacation rentals in Great Barrington

A beautiful, cozy, very well-stocked home. Remote enough to feel like you're in the country but in proximity to so many great activities on offer in Copake and Hudson. A special place. We had a wonderful stay.

Enrique's place was conveniently located near Rhinebeck, but alao far enough away that it was peaceful and quiet. Worth having a drink in the tavern at Beekman Arms and breakfast sandwiches at Rhinebeck Bagels. We especially enjoyed the hot tub. Enrique was a wonderful, informative host, and available if we needed (we didn't). Overall, we had a nice, relaxing weekend.

We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)

This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

We really can’t say enough about Jackie’s place. Beautiful and peaceful surroundings. The home is well appointed and comfortable. The place is so nice we actually cancelled our plans for Saturday night just to stay in and enjoy the vibe. Spent part of the evening just relaxing in the hot tub looking at the amazing night sky!! The kitchen had everything we needed to cook dinner and a nice selection of pots and pans. Would highly recommend. Jackie was very responsive and easy to reach.

We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Full of character and charm, the home is a tranquil retreat where you are surrounded by nature (think morning birdsong & chipmunks in the yard) but also a quick and scenic drive away from the cute town of Woodstock and all the fun and food it has to offer. I love that this home feels like the result of careful craft and curation, with personality and thoughtful details, all down to the art and the kitchen appliances. The co-host, Jon, was communicative, pleasant, generous, respectful and kind. I would highly recommend a stay at this home, and would myself return.

Enjoyed our stay at this Woodstock home on a quiet street. The house was comfortable, laid back and cozy. We walked about 20 minutes to town. Restaurants and stores in town were a treat. All in all a great time.

The loft was lovely: fireplace, large balcony, view down the mountain, TV with airplay support, kitchen, etc. the surrounding was quiet and peaceful. The host was responsive and very friendly. Would recommend to others.

Super close to town! Lovely setting. Fun to take a shower under a skylight. As others have said, it’s very compact! Would be an ideal place for a person to get away to write.

Lovely place in Saugerties, close to lots of great hiking and restaurants.

Donna's place was a wonderful weekend stay! Beautiful property and guest house. Well appointed and care for. Just a few improvements that would have made our stay even better--a small microwave for quick reheating of coffee/leftovers, a luggage rack and place to store/hang clothes, and ensuring the driveway and a walking path are cleared of snow even when out of town (with thawing and refreezing, we had to navigate two inches of solid ice, which was terrifying both on foot and in the car).

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!

A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

What a find! Back apartment to a cute little house. So easy to get to, find, and right near town. Super clean, bright and warm. Pet friendly. Literally checks every box. We hit every local place in town that was on our list and did a quick trip to FDR's home in Hyde Park. 6 stars because 5 just isn't enough.

We stayed here for two nights. It was clean with a lot of space for our family of three. It was an easy and quick walk to the main street in Hudson.

This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

This was our second stay at Susan's home. This is my favorite airbnb. I will always return to Susan's home if we need a getaway. I absolutely love her home. It is so close to nature. The windows look at nature. I could talk and talk about our experience so lets Susan give million stars. I love your home. Thank you, we will stay again.

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

Great place. As described. Met our expectations.

Stayed with 5 children and our dog… this home was super kid and family friendly. The yard was our favorite- fenced in, well taken care of, and the trampoline was a hit. The deck was clean and had comfortable places for lounging. Inside the kitchen had all the amenities needed to cook for ourselves, the space was super clean, and the beds were very comfortable. We would love to visit again!

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

We had a terrific stay. The house was exactly as advertised.

This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!