Kid-friendly vacation rentals in Lenox

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Lenox kid-friendly rentals

Kid-friendly house rentals

Guest favorite
Home in Lee
4.87 out of 5 average rating, 46 reviews

Spacious & Family-Ready Home w/ Fenced Yard in Lee

MauraRating, 5 stars1 month ago
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!
Guest favorite
Home in Richmond
4.94 out of 5 average rating, 18 reviews

Sunshine Cottage

EdRating, 5 stars7 months ago
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.
Top guest favorite
Home in Lenox
5 out of 5 average rating, 22 reviews

Sunny House in Downtown Lenox

MarkRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Lee
4.97 out of 5 average rating, 213 reviews

Berkshire 4 season home

ClaireRating, 5 stars1 week ago
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!
Top guest favorite
Home in Stockbridge
4.95 out of 5 average rating, 132 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

MichaelRating, 5 stars1 week ago
Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!
Top guest favorite
Home in Pittsfield
4.95 out of 5 average rating, 174 reviews

Cantabile life in the Berkshires

BillRating, 5 stars1 week ago
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.
Top guest favorite
Home in Great Barrington
4.99 out of 5 average rating, 122 reviews

Granite Ledge, Modern home in a unique setting

MichaelRating, 5 stars1 week ago
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.
Guest favorite
Home in Great Barrington
4.97 out of 5 average rating, 261 reviews

Jaw dropping mountain & lake views

RobRating, 5 stars1 month ago
Excellent stay at this beautiful house! The views were spectacular and everything was as described in the listing.

Kid-friendly apartment rentals

Guest favorite
Apartment in Plainfield
4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

DouglasRating, 5 stars2 weeks ago
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.
Guest favorite
Apartment in Lenox Dale
4.92 out of 5 average rating, 131 reviews

Charming 2BD apartment.

LindaRating, 5 stars1 month ago
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!
Superhost
Apartment in Philmont
4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

JessicaRating, 5 stars7 months ago
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!
Top guest favorite
Apartment in East Chatham
4.95 out of 5 average rating, 120 reviews

Bennett Abode

AmandaRating, 5 stars1 week ago
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!
Guest favorite
Apartment in Plainfield
4.95 out of 5 average rating, 271 reviews

Sunny carriage house apartment

EllieRating, 5 stars2 weeks ago
We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)
Top guest favorite
Apartment in Troy
4.93 out of 5 average rating, 440 reviews

Stunning studio in the heart of Troy: Raven's Den

BobRating, 5 stars2 weeks ago
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!
Guest favorite
Apartment in Great Barrington
4.88 out of 5 average rating, 104 reviews

Kitchenette|King Bed|Couch

KiriakiRating, 5 stars1 month ago
One of the best accommodations we have stayed at in Great Barrington. We will return!
Guest favorite
Apartment in Pittsfield
4.92 out of 5 average rating, 260 reviews

Marie's Place

DeborahRating, 5 stars4 days ago
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

Guest favorite
Condo in Windham
4.89 out of 5 average rating, 193 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

SuzanneRating, 5 stars1 week ago
Beautiful gem, fantastic hosts. Wouldn’t change a thing. Thank you!
Top guest favorite
Condo in Downtown Hartford
4.99 out of 5 average rating, 127 reviews

Posh Pad in The Business District

JamesRating, 5 stars1 week ago
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.
Top guest favorite
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars3 months ago
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.
Superhost
Condo in Windham
4.73 out of 5 average rating, 280 reviews

Summer Retreat w/ Balcony & inground Pool

AndrewRating, 5 stars4 weeks ago
Was as advertised. Would recommend
Guest favorite
Condo in Center Square
4.9 out of 5 average rating, 268 reviews

Elegant, spacious studio apt in historic mansion

LindseyRating, 5 stars2 weeks ago
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!
Guest favorite
Condo in Dover
4.84 out of 5 average rating, 119 reviews

Walk to Mt. Snow-Spa-Summer Pool

GaryRating, 5 stars2 months ago
Great little studio spot to use as your Basecamp for activities in the area!
Top guest favorite
Condo in Brattleboro
4.93 out of 5 average rating, 353 reviews

Private & Quiet Studio Apt. in Vermont

LynRating, 5 stars2 weeks ago
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.
Top guest favorite
Condo in West Dover
4.92 out of 5 average rating, 123 reviews

3 Story Condo - 5 Minutes to Mount Snow!

AlyssaRating, 5 stars1 week ago
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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