Family-friendly vacation rentals in Lenox

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.

A peaceful location with chill activities for all ages...we enjoyed the phonograph, the retro Atari, the hot tub, the window bird feeder, and watching birds in the spacious yard and conservation area. Herons, hawks, and songbirds viewed. The hot tub was sparkling clean, and the linen robes were a thoughtful touch. Wifi worked great. We arrived late but instructions for entry were crystal clear. Virginia answered my questions promptly and warmly. Definitely a winner.

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.

My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!

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.

It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.

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!

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.

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!

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!

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.

We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.