Kid-friendly vacation rentals in The Berkshires
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in The Berkshires
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires kid-friendly rentals
Kid-friendly house rentals
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
Sep 30 – Oct 7
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Feb 5 – 12
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Sep 14 – 21
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
Dec 20 – 27
Home in Lee
5.0 out of 5 average rating, 231 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr 21 – 28
Home in Cornwall
4.92 out of 5 average rating, 229 reviewsSecluded modern forest cabin with private brook
Aug 1 – 8
Home in New Paltz
4.97 out of 5 average rating, 680 reviewsVictorian Haven
Apr 3 – 10
Home in Lee
4.9 out of 5 average rating, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 30 – Oct 7
Kid-friendly apartment rentals
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Jun 10 – 17
Apartment in Lee
4.79 out of 5 average rating, 107 reviewsCozy Berkshire Cottage Style Apartment
Apr 20 – 27
Apartment in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
Feb 6 – 13
Apartment in Plainfield
4.95 out of 5 average rating, 237 reviewsSunny carriage house apartment
Sep 28 – Oct 5
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Feb 17 – 24
Apartment in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
Nov 1 – 8
Apartment in Brookfield
4.94 out of 5 average rating, 186 reviewsPeaceful apartment on 3.5 acres w/ Artist studio.
Jan 2 – 9
Apartment in Sheffield
4.92 out of 5 average rating, 123 reviewsPrivate Berkshire Barn Apartment
May 24 – 31
Kid-friendly condo rentals
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
May 9 – 16
Condo in Windham
4.89 out of 5 average rating, 133 reviewsCozy Mountain hideaway Windham, Hunter
Sep 22 – 29
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Jun 19 – 26
Condo in Lanesville
4.97 out of 5 average rating, 547 reviewsStylish Condo Ski on/ Ski off Hunter Mountain
Jun 25 – 30
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Feb 24 – Mar 3
Condo in Hunter
4.97 out of 5 average rating, 428 reviews*Great Reviews* Hunter Mtn. Cozy/Clean/Close Condo
Aug 25 – Sep 1
Condo in Middletown
4.97 out of 5 average rating, 104 reviewsEntire place to yourself Cromwell/Middletown Line
Feb 20 – 27
Destinations to explore
- Kid-friendly rentals United States
- Kid-friendly rentals Long Island
- Kid-friendly rentals New York
- Fitness-friendly rentals The Berkshires
- Lakehouse rentals The Berkshires
- Waterfront rentals The Berkshires
- Rentals with a hot tub The Berkshires
- Luxury rentals The Berkshires
- Private suite rentals The Berkshires
- Beachfront rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Rentals with a washer and dryer The Berkshires
- Rentals with breakfast The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with outdoor seating The Berkshires
- Chalet rentals The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Rentals with a kayak The Berkshires
- House rentals The Berkshires
- Wheelchair accessible rentals The Berkshires
- Townhouse rentals The Berkshires
- Cabin rentals The Berkshires
- Apartment rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Hotel rentals The Berkshires
- Pet-friendly rentals The Berkshires
- Cottage rentals The Berkshires
- Rentals with pools The Berkshires
- Rentals with a sauna The Berkshires
- Guesthouse rentals The Berkshires
- Farmstay rentals The Berkshires
- Rentals with a patio The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Condo rentals The Berkshires
- Aparthotel rentals The Berkshires
- Family-friendly rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Rentals with lake access The Berkshires
- Rentals with an EV charger The Berkshires
- Monthly Rentals The Berkshires
- Rentals with a home theater The Berkshires
- Rentals with beach access The Berkshires
- Rentals with a fire pit The Berkshires
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom