Kid-friendly vacation rentals in Lenox

Find and book unique kid-friendly rentals on Airbnb

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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Guest favorite

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lake Retreat-kayaks/SUP/central air

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the bays, coves and creeks -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Superhost

Cottage in Hudson

4.84 out of 5 average rating, 128 reviews

Peaceful waterfront getaway near Hudson, NY

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, Chatham, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount inside an hour. Cozy wood burning stove as well as outdoor fire pit. Minimum 3 day stay.

Guest favorite

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

Cottage in Rhinebeck

4.99 out of 5 average rating, 138 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Guest favorite

Home in North Adams

5 out of 5 average rating, 103 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Guest favorite

Home in Athens

4.83 out of 5 average rating, 169 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

Rental unit in Earlton

4.93 out of 5 average rating, 290 reviews

Sweet Farm Stay

Come stay in a fully-outfitted barn apartment with views that look out over the pony paddock and the sheep pasture! For an extra fee we also offer… ** FARM CAMP** perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning that you are here. ** CRAFT RETREATS** All-inclusive weekend with up to 7 guests. Wool / wood / kitchen craft. Work on the farm, MAKE stuff, and enjoy the outdoors. DM for more info. Find us on ig — honeyhollowfarmstay!

Guest favorite

Bungalow in Great Barrington

4.91 out of 5 average rating, 116 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Guest favorite

Cabin in Catskill

4.96 out of 5 average rating, 252 reviews

Catskills Log Home, Stunning Mountain Views

This Catskills log home, with its privacy and stunning views, provides an ideal hub for a getaway! A two hour drive from NYC—with nearby getaways for skiers, hikers, and antiquing—this home now includes a massive deck expansion and 6 person Marquis hot tub for couples looking for the perfect way to relax. The house is lovingly cared for; three bedrooms are furnished with new and comfortable bedding and sectional for 6. Visit us and take in the fresh country air!

Guest favorite

Home in Hillsdale

4.91 out of 5 average rating, 114 reviews

Fenced yard, playroom & the Berkshires - $0 fees

Enjoy our 8.5 acre, private home. It's a great place to either relax, or enjoy nature whether it's skiing, hiking, kayaking, or biking. Ample space for numerous groups, including an enclosed backyard with grill and fire pit. 4 bedrooms and 3 baths For hikers, Taconic State Park :06 For bikers, Harlem Vally Rail Trail :08 For skiers, Catamount :05 ~2.5 hours from NYC and Boston ~ 15 min to Great Barrington, MA ~25 min to Hudson, NY ~20 min to Millerton, NY

Guest favorite

Cabin in Catskill

4.9 out of 5 average rating, 186 reviews

Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill

Experience the beauty of the great outdoors while also enjoying modern comforts in this newly renovated A-frame cabin style home. This peaceful location away from the hustle and bustle is still easily accessible without a car and only a 10 minute taxi drive from the nearest station (Jeffersons Lines) The elegantly finished interiors continue to be upgraded by the owners who love combining modern touches with the stunning natural surroundings of the area.

Superhost

Tiny home in Nassau

4.94 out of 5 average rating, 141 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays are welcome! *** IMPORTANT *** Our photos previously showed screens enclosing the porch, but we have removed them due to wear from pets. Maintaining a pet-friendly environment is important to us, so the screens are no longer part of the tiny house. Enjoy a stay in our clean, charming, unique tiny home. This waterfront property features a private peninsula with a sandy entrance to the water.