Family-friendly holiday rentals in Berkshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Berkshire County
Guests agree: these family-friendly homes 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
Family-friendly home rentals with a hot tub
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
24–31 Dec
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
9–16 Oct
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
19–26 Mar
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
5–12 Mar
Home in Hancock
4.85 out of 5 average rating, 41 reviewsJiminy Peak Peaceful Home in Berkshires
6–13 Feb
Home in East Chatham
4.78 out of 5 average rating, 172 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
21–28 Sep
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
15–22 Jul
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot tub Tennis Court&Pool
23–30 Jun
Family- and pet-friendly home rentals
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
28 Sep – 5 Oct
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
6–13 Feb
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
31 Oct – 7 Nov
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
28 Nov – 5 Dec
Farm stay in New Ashford
4.9 out of 5 average rating, 221 reviewsSheep Barn on the Greylock Valley Estate
24 Feb – 3 Mar
Home in Williamstown
4.81 out of 5 average rating, 171 reviewsWalking distance to downtown
11–18 Apr
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
24 Sep – 1 Oct
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
10–17 May
Family-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
24 Nov – 1 Dec
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
25 Sep – 2 Oct
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
1–8 Dec
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
1–8 Nov
Home in Stockbridge
4.85 out of 5 average rating, 62 reviews*February/March Special*"Too Good" AKA 2 Goodrich
18–25 Nov
Home in Stephentown
4.9 out of 5 average rating, 10 reviewsBerkshire Beauty
6–13 Oct
Home in Sandisfield
4.96 out of 5 average rating, 24 reviewsPrivate gem in the Berkshires on the Buck River
20–27 May
Home in Canaan
4.99 out of 5 average rating, 68 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
7–14 Dec
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals Massachusetts
- Family-friendly rentals Massachusetts
- Ski-in/ski-out rentals Berkshire County
- Rentals with a firepit Berkshire County
- Cottage rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Bed and breakfasts Berkshire County
- Flat rentals Berkshire County
- Rentals with pools Berkshire County
- Private suite rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with lake access Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Rentals with breakfast Berkshire County
- Fitness-friendly rentals Berkshire County
- Beachfront rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Boutique hotel rentals Berkshire County
- Cabin rentals Berkshire County
- Farm stay rentals Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Guest house rentals Berkshire County
- Rentals with a patio Berkshire County
- Chalet rentals Berkshire County
- Waterfront rentals Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with outdoor seating Berkshire County
- House rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Hotel rentals Berkshire County
- Rentals with beach access Berkshire County
- Monthly 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