
Kid-friendly vacation rentals in Lenox
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Top-rated kid-friendly rentals in Lenox
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Lenox kid-friendly rentals
Kid-friendly house rentals

Spacious & Family-Ready Home w/ Fenced Yard in Lee
We had a great stay! Vinicius’s home was clean, conveniently located to explore the Berkshires and easily accommodated our party of four, plus a dog. The fenced-in yard came in very handy with the latter!

Sunshine Cottage
We only stayed one evening but found the living space to be perfectly laid out and spotless. The kitchen is fully stocked with about every utensil and appliance you can think of. We especially enjoyed the fresh eggs, treats, and flowers that welcomed us! The living room was especially comfortable. The unit is attached to the rear of the main house but it’s kept totally private. There aren’t many places to eat in Richmond — after all, it is pretty rural— but Stockbridge and Lennox offer many dining options.

Sunny House in Downtown Lenox
We loved this place. Everything is as described. It’s within walking distance of the main section of Lenox with restaurants and such, but still a block back into a lovely neighborhood so it felt secluded. No traffic or sounds of people. Very quiet.

Berkshire 4 season home
John and Angela are incredible hosts and we’re so kind to us. They very clearly care about their guests and we are excited to stay here again. Their home had all the “creature comforts” someone traveling can ask for. Comfy linens, stocked bathrooms, fully stocked kitchen, large living spaces, and a great backyard space. Total gem!

Sun-filled, Charming Stockbridge Classic- In Town!
Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!

Cantabile life in the Berkshires
Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.

Granite Ledge, Modern home in a unique setting
Had a wonderful time at Granite ledge. Absolutely beautiful backyard. Very peaceful and comfortable. The bed was very comfortable and we slept like babies. Highly recommend and would definitely stay here again.

Jaw dropping mountain & lake views
Excellent stay at this beautiful house! The views were spectacular and everything was as described in the listing.
Kid-friendly apartment rentals

Sunny, light filled loft in 1873 Colonial
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

Charming 2BD apartment.
This place is a gem! The apartment has 2 private entrances, plus a parking spot that is visible from the apartment above. It is conveniently located near major stores, restaurants, and an EV charging station. My daughter and I stayed for 2 nights because we were attending a wedding in Tanglewood, just a few minutes away! The apartment was spotless, well stocked with linens, bathrobes, paper products, Keurig coffee pods, and the refrigerator even had chilled beverages! The kitchen is equipped with modern appliances and everything needed to prepare meals. There is even a stackable washer/dryer with laundry pods. The 2 bedrooms are far away from each other to afford privacy. The beds are extremely comfortable with high-quality sheets and comforters, plus extra pillows and blankets in drawers and closets. Our Superhosts, Richard and Kathleen, were extremely responsive to our needs and provided great recommendations for nearby restaurants and stores. Our stay was 100% PERFECT!

Beautiful space in the heart of Philmont
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

Bennett Abode
We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!

Sunny carriage house apartment
We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

Stunning studio in the heart of Troy: Raven's Den
Perfect night for a nearby getaway while things done at my apartment. Lot of charm and everything you could need is in this den. Pictures did it justice. I’ll stay again just for the fun of it next time. Igor was easy to communicate with and he was spot on with everything he has posted on the listing. This place is a gem!

Kitchenette|King Bed|Couch
One of the best accommodations we have stayed at in Great Barrington. We will return!

Marie's Place
My Mom and I loved Marie’s home. So clean and light with lots of windows. Beautiful porch to sit at end of day Slept so well. We would love to stay there again I was in need of help with tv and they came within 15 min Unbelievable how helpful and kind Thank you so much Deb
Kid-friendly condo rentals

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.
Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!

Posh Pad in The Business District
Obinna is a great host and this apartment is so comfortable and lots of space to stretch out. Fully stocked kitchen and there are fantastic restaurants within walking distance. Two 65", high end tvs and the mattresses on the beds are sooo nice. Obinna puts effort in where a lot of hosts cheap out, which really makes this pad special. It's tough to get an open spot here on the calendar, but, if get the chance, make your reservation here. It's the best in the area.

Summer Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Summer Retreat w/ Balcony & inground Pool
Was as advertised. Would recommend

Elegant, spacious studio apt in historic mansion
Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!

Walk to Mt. Snow-Spa-Summer Pool
Great little studio spot to use as your Basecamp for activities in the area!

Private & Quiet Studio Apt. in Vermont
We are repeat visitors. Staying here is always a pleasure. The apartment is wonderful. Just as described and perfect for day trips or just staying in. Mary and Lance are friendly and courteous. Hope to be able to stay here again when in the area.

3 Story Condo - 5 Minutes to Mount Snow!
It was such an easy check in and check out process. He let us check in an hour early since we arrived earlier. Place is spacious and exactly as described. Highly recommend!
Quick stats about vacation rentals that are kid-friendly in Lenox
Total rentals
30 properties
Nightly prices starting at
R1,257 ZAR before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Windham Mountain
- Albany Center Gallery
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hunter Mountain Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag