Family-friendly vacation rentals in Lenox

We had a wonderful time at Mirav’s place in Woodstock. Made great use of the hot tub and the fireplace. We absolutely plan on returning soon!

We enjoyed our 2-night stay at Enrique's Rhinebeck home. It's out in the country, very peaceful, and very quiet at night. About an 8 minute drive to the charming town of Rhinebeck. We were out riding the rail trails during the day, but when at the house, really enjoyed the deck, hot tub, and screened porch (later at night when it got buggy). The kitchen is well appointed. Bedrooms and bathrooms are on the smaller side. Definitely would consider staying here again if ever back in the Rhinebeck area.

We had a great time staying at Joann’s place! We came here with a group of friends from college and it was a perfect spot to hang out, play board games and a not far from some great hikes (would highly recommend Kaaterskill Falls Laurel House trail). The hot tub is great and the backyard is an awesome place to hang out. Joann was super communicative and responsive and went above and beyond to help with any issues as they arose. Would highly recommend her to anyone!

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!

Fantastic place. My adult children had a blast playing basketball and tennis. The pool table and piano were thoroughly enjoyed --piano sounded well tuned. Views out of living room are particularly stunning. Hot tub was also great amenity and great after long day. Tons of toys for my grandson to enjoy. We cooked incredible meals and there were plenty of supplies for that. Highly recommend fur faculty reunion or sporty families. Near to everything

Had a lovely weekend getaway here! Mirav’s place was clean and quiet, and everything was as described. We enjoyed the hot tub and the close proximity to Woodstock; it’s less than a 10 minute drive, so easily accessible for good food and cute shops. Would definitely stay again!

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!

The house was extremely cozy and felt like a true ski house. It was fully stocked from cookware to card games and plenty of space to feel comfortable away from home. Alana was extremely pleasant to talk to and responded quickly to any of my questions. For our long stay, they had cleaners come to the home for an intermittent cleaning. As well as having the driveway plowed and salted after snow storms. The 15 min commute to mount snow is convenient and easy to navigate. I highly recommend staying for the great hospitality and the lovely home. I can’t wait to stay again.

This is the place to go if you want to be immersed in nature. You are definitely in the woods and surrounded by lush green. There is a pond glistening in your view from the back screened in porch. A lovely spot to have a curl up with a good book.!

Beautiful quiet private setting. Everything as advertised, clean, and great communication throughout. Would definitely stay there again! Thanks so much for a beautiful stopping place on our travels!

Location and space worked out perfectly for our little surprise birthday party. Clean, comfortable, spacious. Charming old farmhouse.

What a beautiful space to book! All pictures are exactly as joe displayed. Joe and his team we're nothing but a first class operation, even with a short notification of our plans to stay. I would highly recommend this space or any location that Joe offers.

This house was perfect for our family with adult children and an old dog; it was clean and spacious, and yet homey. We felt comfortable right away. The view of trees and Overlook Mountain is stunning, and the house is truly secluded, and yet close to town. Simply terrific!

We rode across the state on motorcycles, which made for a long and borderline miserable day, and were very happy to finally land at Niall and Clare's home for a couple of days. The listing was very accurate and their suggestions and instructions were very helpful. Niall ended up helping us with usage/instructions for their nice Weber grill (it was easy), and we also made breakfast in the mornings. Everything was clean and neat and very homey and I would love to stay here again in the future. We also enjoyed a really nice "Irish Alps" experience around the corner at the Shamrock with a circle of folks with instruments singing and laughing together in the barroom.

If it’s available- book it! Worth every penny. First, the house is gracious with plenty of gathering space to watch TV, listen to music (lps included), work on some puzzles, or chat with your friends and family. There are even three different areas to eat. Then, we were surprised by the quiet sitting space in each bedroom as well! The host is attentive and helpful, with clear instructions to make your stay easy and enjoyable. There were toys for the little ones, and an amazing porch for morning coffee and evening wine. You can walk left down the street to a path through the fields, or turn right and see the largest Sycamore this side of the Mississippi! We had two kids graduating at UMASS Amherst and with three days of events, it was perfect, especially getting to campus on the Northeast side- if you know, you know… This big old home became the perfect setting for our family memories! Thank you!

Charming historic house with great view in a secluded area. More room than I expected and comfortable. Kids had fun feeding the animals. Glad we discovered the hut and stage nearby. Looks like a nice spot to come back during warmer weather for camping and more trail exploration.

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!

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 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.

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.

I’d highly recommend this accommodation! House is exactly as pictured and just lovely. Great location. PARKING!! Space for us in the driveway! There were 3 of us, all adults and we had more than enough space. Beds were comfy and huge couch perfect for napping. Would highly recommend and hope to get back there soon. Didn’t get to use pool (crummy weather) but it looks lovely.

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 👍🏼