Family-friendly holiday rentals in Lenox

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.

Choosing to stay in Porter's container cabin was the best decision we could have made for our vacation. It was so peaceful and relaxing. We had daily visits from a beautiful deer, and countless butterflies. We chose to use this time to unplug, and really connect with each other, and we could not have chosen a better place to spend our time. We've missed the view from the front door every day since we've left, and we're already planning to come back next year. Thank you so much for having us.

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.

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.

Mary's home was exactly what we hoped for - on a mountain, beautiful scenery, clean, comfortable and quiet! Although we only had two days, it felt like time slowed down while we were there. The views, the hot tub, the comfortable furniture and tasteful decor were all wonderful. AND we were able to bring our dog, Ruah! We hope to visit again in the future! Thank you, Mary & Tim!

We were very comfortable at King’s Cottage. We had everything we needed. It was so quiet, private, comfortable and well appointed. Messages from the host were friendly and helpful. Great stay in a beautiful spot!

Ilze and Laurence’s place felt like home away from home. Every morning, we were greeted with chirping birds, clucking hens (was even able to order a dozen eggs straight from their free-range poultry—so organic!)—and a smiling donkey! It is a place were you can find peace and rest for your soul even for just a few days.

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!

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!

We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!

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!

Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

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 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!!

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

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

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

My family stayed here for a weekend trip to Windham. The location to the ski area was very close, only 6 minutes away. There were plenty of nearby restaurants, markets, and coffee. The house is clean and cozy and perfect for a family of 4 or 5.

We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼