Family-friendly holiday rentals in Pittsfield

Three adults and a toddler spent four great days at Myrhah’s house in Craryville. I have very little to add to all the other enthusiastically positive reviews. They are totally accurate.I will note that one of us is a pastry chef who was at home in Myrhah’s kitchen. It’s stocked with quite a few good baking tools. Another member of our group is a 19-month old toddler who loved the toys and big airy spaces for play. We all enjoyed the home’s aesthetic and appreciated Myrhah’s responsiveness and warmth. I wished we could have stayed longer.

Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.

This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

We really enjoyed staying here, only wish we booked it for longer! Our son and our dog enjoyed going for walks on the trails behind the brewery. The beers and pizza from the brewery were excellent, the house is really charming and relaxing. Also got out to enjoy the disc golf course which was a fun way to spend the afternoon. I would love to come back and try out the mountain bike trails. The surrounding area was fun to explore, really can't think of any negative points to this place!

We loved staying at Anat’s gorgeous home. We’ve been in many spots in the HRV and even Columbia County, but this stood out for being so tranquil and for having such lovely grounds. We enjoyed the Copake Hillsdale Farmers Market and a great meals at Local 111 and Zinneas. Cooking at the house was a breeze and there were more than enough beds and living spaces for our two families to feel so comfortable. Hot tub was lovely! We can’t wait to return.

We had a wonderful stay at this property on Memorial Day Weekend! Everything in the home was exactly as described and comfortable. We didn’t have that much time to enjoy the clubhouse but we hope to return for a longer stay and take advantage of all it had to offer. The staff there were so wonderful and accommodating and gave us a wonderful tour.

Another perfect stay at Laurie's. This is our third stay over Thanksgiving week and we always are sad to leave. My family absolutely loves staying here. There is plenty of room to gather or to have some alone time. Beds are comfortable. Kitchen has everything you could need and is always pristine. Check in is stress free. Area is peaceful and serene. Lee is a lovely New England town. Downtown is less than a 5 minute ride. Many restaurants within a 5-20 minute ride. Outlets are 10 minutes away. Looking forward to our stay next year.

This was a perfect spot for my family's gathering to remember my brother. Because of the rapid gentrification of this city it has been difficult to find housing and space in general for community gatherings, but this worked out beautifully and was an ideal setting for such an important event. The space is very beautiful and clean and the host was generous and gracious. Thank you!

Laurence and Ilze were incredible hosts, incredibly helpful and responsive, going above and beyond to sort out our needs. The house was as advertised and we had a a great time at their place. Should we be back in the area we’d definitely try to stay with them again!

Great location for exploring nearby towns like Northampton, Amherst, Shelburn falls. As Laura said, no cell service in this town but their WiFi worked great in the unit and it’s a quite peaceful area to stay. The home feels like a well maintained cabin. It’s rustic and cozy but you might find a spider in the shower. I did not find the beds very comfortable but otherwise had a very relaxing stay. Laura was a great host and very responsive

Staying at Will and Aenne's barn house was fun and wholesome. I enjoyed saying hello to the animals and the jungle shower most of all. The barn has everything one needs. Though, I must say I was very intimidated by having to light the chef's stove. We walked from the barn to the waterfall down town which was beautiful--great place to hang out and swim in the warmer months. The village of Kinderhook is adorable with quaint little shops. Hudson city had some of the best food I've had in a long time; I strongly recommend eating at Cafe Mutton. Overall, Will and Aenne were very hands-off hosts--as in, they gave us our space and privacy--while still being responsive and attentive. Thank you for the stay! I hope to come back again!

The airbnb was close to town. The house was very clean and comfortable.

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

Had an absolutely wonderful stay at Lena’s place. Very quiet, very serene— but close enough to downtown Hudson for when I wanted a night out. The dogs absolutely loved our walks up the long scenic (and completely private) driveway. The cat adored birdwatching from the sliding doors. We will definitely be coming back!

The house is so beautiful and unique, and there is art everywhere you look. It inspires creativity! The hot tub and pool are incredible. The house has everything you need to feel at home. It's quiet and peaceful, and the view is out of this world. This is such a wonderful place for a getaway. Our family had a great time, and we can't wait to visit again soon! Olia made sure we had everything we needed and provided great suggestions for things to do in the area. It was an amazing holiday getaway!

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

This is our fifth year coming to the farm. Larissa is absolutely masterful with kids of all ages (even tough kids). My daughter races out at 9 am to do farm chores and begs for more (and this is a kid who drags her feet doing chores at home)!! We love the rhythm of farm and find it really easy to disconnect and unwind. After chores in the morning, you're welcome to spend as much time as you want with the animals, which is a real treat. Whether it's feeding the horses hay, sharing food scraps with the goats, or watching the chickens do their evening routine, there's so much to enjoy. The local towns are lovely, but if you like the farm experience, you may never leave the property. Larissa is incredibly knowledgeable and generous in sharing her experience and expertise. She has created an absolutely magical environment, and I would highly recommend visiting!!

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!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

We had a great time at Saugerties! Rebecca's house was wonderful. The heated pool and the trampoline were the kids' favorite and they kept them entertained all day. The adults enjoyed the shade under the comfy pool lounge chairs & the spacious deck furniture. The backyard of the house was well kept and equipped so we spent a lot of time outside. The house is very well equipped and it was spacious for 2 families of 4. Everything was functioning well. The house is close to downtown and there are plenty of things to do nearby. Host was super quick to respond back and to help with whatever we needed right away. We def recommend Rebecca's house.

Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.