Family-friendly vacation rentals in Pittsfield

A quiet private property located close to amenities, the city of Hudson, and nature. It is a beautiful and comfortable home filled with creative and tangible care. We enjoyed cooking in the kitchen and spending time on the property over a long weekend stay.

Loved this house! We have stayed in many places all over the world for both business and pleasure. This was a business trip. House was great, location was great. It was cold and rainy so we didn’t get to enjoy the porch, deck or hot tub . Even without these amenities we totally enjoyed the house. Hoping to stay again next time we are in the area. We are in Rhinebeck twice a year for the antiques show in the Fairgrounds . Instructions on house were easy to understand and concise. Great job guys!

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.

We had a great and easy stay for a quick upstate weekend! The house was clean, cute, and accommodated our family of 7. We unfortunately didn’t get to utilize the outdoors because of the weather. Would definitely recommend this house!

Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.

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.

The house perfect for what we needed. Plenty of space to spread out. Had everything we needed. Host was responsive when we needed anything. Will stay there again for sure. Great place.

Our stay with Lars was beautifully pristine and the perfect place to relax in Vermont. This was one of our favorite airbnbs ever and we can’t wait to come back. Lars is great, responsive, and friendly. Lars’s place has a beautiful kitchen and bathroom and an incredibly cozy bedroom. No words can describe how lovely and relaxing this cute rugged airbnb is!

I think this was our fifth stay at Laurie's place, which shows how much we like it. It's perfect when we visit with family, because there is plenty of space for everyone. We didn't really take advantage of it this time, but having the full kitchen is nice. We're usually there in the winter, but one day I hope to be able to enjoy the porch and the deck.

This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!

The guesthouse was so dreamy! We had a wonderful stay, the hosts were super friendly, and we loved meeting their sweet dogs. The house was close to great restaurants and shops in Hudson, Kinderhook, and Ghent, as well as hiking trails. The lovely trail on the property was a great bonus, one we took advantage of 4 times throughout the weekend :). Would definitely visit again!

Our family loved our stay at this house. It is a peaceful and serene setting in a beautiful wooded area. The host was very accommodating on short notice. The house has a very nice and inviting interior, it feels very homey and comfortable. There are many nice places for a hike and the view at the top of the hill on the property is quite scenic, we could see the Catskills to the south. There are all the modern amenities, and the (decorative) antique wood burning stove in the kitchen was a neat touch. I would definitely recommend this place!

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!

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!

Bobby was the ultimate host in every way. I felt so relaxed and comfortable in his home that I extended my stay for another week and have already booked for a future stay. The home is beautiful, full of original art, cozy and perfectly suited for a quiet getaway yet close enough to Hudson, Kinderhook and Catskill. The house gets beautiful morning light and I found it very relaxing having my morning coffee on the sun porch. The flowers and trees were just starting to bloom in the garden - making it the perfect canopy for my guests and I to have an early evening cocktail before heading into town for dinner. Very much looking forward to returning in a few months!

We loved staying here at Matthew’s Barn House. The location is not only peaceful and private, but we were able to completely unplug from our busy lives and enjoy time with our family.

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!

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

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

Great hosts that make you feel right at home. We were greeted with some extra special touches that we were not expecting during our stay, that was very thoughtful. The space is exactly as pictured and very comfortable. We would definitely come back

This was our second stay at the Queechy Lake house and it did not disappoint! The home is wonderfully maintained, fully equipped and cozy - we appreciated the new additions of the pool and backyard activities. It rained most of the weekend but we utilized Meredith and Jason’s local recommendations and had a blast.

We had a wonderful time at Tina’s place! Surrounded by woods, but somewhat close to the downtown area (super cute too!), the cabin had all we needed, and is also very cozy, neat, comfortable. Excellent bed and pillows, perfectly AC’d, with a fully stocked kitchen. We are happy, and our pups were THRILLED! Huge thanks to the host.