![](https://a0.muscache.com/im/pictures/1ff6d909-5ba6-42f3-9d2c-fa2327780936.jpg)
Kid-friendly holiday rentals in Berkshire County
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Berkshire County
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County family-friendly rentals
Kid-friendly house rentals
![](https://a0.muscache.com/im/pictures/2524e0bf-821e-440f-ad41-c76d62c99756.jpg?im_w=720)
Home in Lee
5 out of 5 average rating, 238 reviewsBerkshire Mountain retreat with Urban eco-luxuries
![](https://a0.muscache.com/im/pictures/6d97db94-744a-4889-8ca5-eb728f4c361d.jpg?im_w=720)
Home in Huntington
4.91 out of 5 average rating, 117 reviewsPrivate house on the River
![](https://a0.muscache.com/im/pictures/3bcc8b89-76a7-40d0-b94b-e99892c24e6f.jpg?im_w=720)
Home in Becket
4.93 out of 5 average rating, 101 reviewsBeautiful, quiet and cozy home in Becket!
![](https://a0.muscache.com/im/pictures/682a4e8c-107d-4bc7-9f68-22070bea55fe.jpg?im_w=720)
Home in Becket
4.87 out of 5 average rating, 299 reviewsReal Estate:Therapy - Lake, Laundry, Love it
![](https://a0.muscache.com/im/pictures/1bd16c5e-305b-4b07-b31e-8d3446bceec7.jpg?im_w=720)
Home in Chester
4.96 out of 5 average rating, 322 reviewsRiverfront Getaway
![](https://a0.muscache.com/im/pictures/ec1d904e-2c79-486c-bcf0-e5d698968c2c.jpg?im_w=720)
Home in Dalton
4.99 out of 5 average rating, 130 reviewsCleveland House - renovated Berkshires' gem.
![](https://a0.muscache.com/im/pictures/466ff970-05a5-415c-ae40-1c6921333851.jpg?im_w=720)
Home in Egremont
4.97 out of 5 average rating, 117 reviewsA sunny, quiet chalet beautifully decorated.
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MTY1NDQ4NjU%3D/original/28164a65-3062-4213-8574-93efc9feb475.jpeg?im_w=720)
Home in Lenox
4.93 out of 5 average rating, 220 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Family-friendly apartment rentals
![](https://a0.muscache.com/im/pictures/9915708a-5cc6-4f4f-9ef0-70338767cb59.jpg?im_w=720)
Rental unit in Sheffield
5 out of 5 average rating, 333 reviewsHideaway with Spectacular Berkshire Views
![](https://a0.muscache.com/im/pictures/6c71c167-d0bb-4d8e-a3c6-27681cb339d8.jpg?im_w=720)
Rental unit in Great Barrington
5 out of 5 average rating, 102 reviewsWalk Everywhere! | Relax in Easy Elegance!
![](https://a0.muscache.com/im/pictures/84113b6c-8ea8-4ee9-becf-fd5f39fc809b.jpg?im_w=720)
Rental unit in Sheffield
4.92 out of 5 average rating, 129 reviewsPrivate Berkshire Barn Apartment
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MjU4ODU1NzI%3D/original/d260ec7e-01c0-4729-be4d-4244e8b4f67d.jpeg?im_w=720)
Rental unit in Williamstown
4.93 out of 5 average rating, 256 reviewsCOLD SPRING
![](https://a0.muscache.com/im/pictures/ab4292b4-19e0-4556-8fc9-83047c1fb050.jpg?im_w=720)
Rental unit in North Adams
5 out of 5 average rating, 126 reviewsWhiteley Hideaway- walk to Mass MoCA and Downtown
![](https://a0.muscache.com/im/pictures/1793c6a4-90b4-4987-b644-b43c59c4a421.jpg?im_w=720)
Rental unit in Lee
4.78 out of 5 average rating, 113 reviewsCozy Berkshire Cottage Style Apartment
![](https://a0.muscache.com/im/pictures/miso/Hosting-864074/original/8bfe14c0-a397-4a5b-8b16-a914acc40ce3.jpeg?im_w=720)
Rental unit in North Adams
4.95 out of 5 average rating, 719 reviewsGuest Apt. Near MCLA & MASS MoCA
![](https://a0.muscache.com/im/pictures/airflow/Hosting-6018524/original/f811ed9e-c648-46af-87bd-b38480fb1bf9.jpg?im_w=720)
Rental unit in North Adams
4.98 out of 5 average rating, 184 reviewsOverlooking the city in a quiet 7 unit building.
Family-friendly apartment rentals
![](https://a0.muscache.com/im/pictures/miso/Hosting-21277776/original/6354ed9d-2f8d-4f27-84b3-43f4730dd34f.jpeg?im_w=720)
Apartment in Hancock
4.84 out of 5 average rating, 134 reviewsCozy Condo @ Jiminy Peak
![](https://a0.muscache.com/im/pictures/miso/Hosting-725392290109371846/original/4c8129c2-0a30-4113-9acf-32de913fd43e.jpeg?im_w=720)
Apartment in Hancock
4.96 out of 5 average rating, 23 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
![](https://a0.muscache.com/im/pictures/6a30f196-7314-4b85-8a91-af48e23ce5aa.jpg?im_w=720)
Apartment in North Adams
4.95 out of 5 average rating, 40 reviewsNewly renovated 2BR on historic Eagle Street.
![](https://a0.muscache.com/im/pictures/a413c7da-f2a8-45e0-bdc7-b8cfb7ab561e.jpg?im_w=720)
Apartment in Hancock
4.91 out of 5 average rating, 54 reviewsJiminy Peak Country Inn - ski in/out condo MT view
![](https://a0.muscache.com/im/pictures/miso/Hosting-35060749/original/5663bb26-36e5-4040-9cba-5ba4dda1ba61.jpeg?im_w=720)
Apartment in Hancock
4.92 out of 5 average rating, 25 reviewsAll-season Berkshires ski resort condo - Sitzmark
![](https://a0.muscache.com/im/pictures/9bf2f3e1-e4a3-4839-bb18-d3a5844cde6f.jpg?im_w=720)
Apartment in Hancock
4.94 out of 5 average rating, 17 reviewsLarge one bedroom, two full bath, full kitchen
![](https://a0.muscache.com/im/pictures/2e33b16d-69e4-4b36-8e2c-221b084c2418.jpg?im_w=720)
Apartment in Lenox
5 out of 5 average rating, 21 reviewsSpacious 3 bedroom apt in Lenox historic downtown
![](https://a0.muscache.com/im/pictures/miso/Hosting-24713146/original/b1ebde23-5341-48f8-8bca-31ee3223cfd7.jpeg?im_w=720)
Apartment in Hancock
4.97 out of 5 average rating, 38 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with pools Berkshire County
- Pet-friendly rentals Berkshire County
- Waterfront rentals Berkshire County
- Rentals with a patio Berkshire County
- Beachfront rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Fitness-friendly rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- House rentals Berkshire County
- Rentals with a sauna Berkshire County
- Flat rentals Berkshire County
- Chalet rentals Berkshire County
- Boutique hotel rentals Berkshire County
- Rentals with lake access Berkshire County
- Cottage rentals Berkshire County
- Bed and breakfasts Berkshire County
- Monthly Rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Hotel rentals Berkshire County
- Guest house rentals Berkshire County
- Rentals with a kayak Berkshire County
- Farm stay rentals Berkshire County
- Rentals with a firepit Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with a fireplace Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Rentals with beach access Berkshire County
- Private suite rentals Berkshire County
- 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