Skip to content

Family-friendly vacation rentals in Berkshire County

Find and book unique family-friendly homes on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated family-friendly rentals in Berkshire County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
Sep 7 – 14
$352 per night
4.94 out of 5 average rating, 341 reviews
Guest favorite
Loft in Great Barrington
The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.
Apr 22 – 29
$139 per night
4.99 out of 5 average rating, 293 reviews
Guest favorite
Guesthouse in Becket
Country Cabin
Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.
Apr 5 – 12
$106 per night
4.93 out of 5 average rating, 256 reviews

Popular amenities for Berkshire County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
Apr 27 – May 4
$298 per night
4.95 out of 5 average rating, 246 reviews
Guest favorite
Cabin in Becket
Waldtreff - quiet grand cabin
May 7 – 14
$219 per night
5.0 out of 5 average rating, 253 reviews
Guest favorite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
Nov 18 – 25
$389 per night
4.83 out of 5 average rating, 161 reviews
Guest favorite
Home in Lee
Spectacular Berkshire Retreat on Private Lake
Oct 1 – 8
$575 per night
4.96 out of 5 average rating, 75 reviews
Guest favorite
Home in East Chatham
Hot tub in Berkshires! 3 Queen 2 Bath! Windswept!
May 8 – 15
$203 per night
4.79 out of 5 average rating, 167 reviews
Cottage in Becket
A Magical Spot on Little Robin Lake
Jun 10 – 17
$212 per night
4.6 out of 5 average rating, 143 reviews
Cottage in Becket
Berkshires Cottage Retreat - Private Hot Tub
May 8 – 15
$144 per night
4.67 out of 5 average rating, 333 reviews
Guest favorite
Chalet in Richmond
Updated Berkshires Chalet Mins to Tanglewood/Lenox
Jan 22 – 29
$431 per night
4.98 out of 5 average rating, 86 reviews
Home in Lenox
Luxury Fox Hollow Home-Laurel Lake
Sep 14 – 21
$511 per night
4.73 out of 5 average rating, 73 reviews
Home in Lanesboro
My Mountain Haven- The Perfect Escape
Nov 22 – 29
$245 per night
4.95 out of 5 average rating, 19 reviews
Chalet in Monterey
Stunning Log Cabin
Aug 20 – 27
$629 per night
5.0 out of 5 average rating, 10 reviews
Condo in Williamstown
Vacation Village in the Berkshires Resort Suite B
Jan 16 – 23
$180 per night
New place to stay

Family- and pet-friendly home rentals

Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
Oct 27 – Nov 3
$241 per night
4.85 out of 5 average rating, 246 reviews
Guest favorite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Apr 26 – May 3
$300 per night
4.92 out of 5 average rating, 167 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
4.83 out of 5 average rating, 151 reviews
Guest favorite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
Jan 22 – 29
$338 per night
4.85 out of 5 average rating, 196 reviews
Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
May 9 – 16
$301 per night
4.81 out of 5 average rating, 243 reviews
Guest favorite
Guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
Oct 28 – Nov 4
$144 per night
4.93 out of 5 average rating, 166 reviews
Guest favorite
Cabin in Lee
Spring fever! Cabin with views in the Berkshires
May 14 – 21
$290 per night
4.9 out of 5 average rating, 102 reviews
Guest favorite
Home in Great Barrington
Your own private Berkshires retreat
Sep 29 – Oct 6
$263 per night
4.9 out of 5 average rating, 111 reviews
Superhost
Cottage in Canaan
Plan your Berkshires by the lake
Apr 1 – 8
$194 per night
4.9 out of 5 average rating, 125 reviews
Guest favorite
Apartment in Great Barrington
Secluded but not isolated Berkshire Retreat
Jun 21 – 28
$159 per night
4.93 out of 5 average rating, 177 reviews
Guest favorite
Home in Williamstown
Walking distance to downtown
Feb 5 – 12
$132 per night
4.8 out of 5 average rating, 166 reviews
Guest favorite
Apartment in Sandisfield
Sunny Berkshire Studio Apartment
Jan 14 – 21
$105 per night
4.92 out of 5 average rating, 227 reviews

Family-friendly home rentals with a pool

Guest favorite
Guesthouse in Williamstown
Perfect Base for Your Berkshire Adventure
Aug 5 – 12
$145 per night
4.93 out of 5 average rating, 219 reviews
Guest favorite
Condo in Hancock
Cozy Condo @ Jiminy Peak
Aug 9 – 16
$150 per night
4.83 out of 5 average rating, 129 reviews
Guest favorite
Bungalow in Williamstown
Hollywood Bungalow in the Berkshires
Dec 10 – 17
$204 per night
4.89 out of 5 average rating, 201 reviews
Guest favorite
Home in Sheffield
Race Mountain House
May 2 – 9
$483 per night
4.85 out of 5 average rating, 114 reviews
Guest favorite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Oct 2 – 9
$925 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Dec 14 – 21
$700 per night
4.99 out of 5 average rating, 68 reviews
Guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
Oct 27 – Nov 3
$743 per night
4.97 out of 5 average rating, 34 reviews
Guest favorite
Home in Hancock
Jiminy Peak Peaceful Home in Berkshires
Feb 11 – 18
$432 per night
4.85 out of 5 average rating, 41 reviews
Superhost
Home in Stockbridge
Private Berkshire County Retreat
Feb 24 – Mar 3
$299 per night
4.85 out of 5 average rating, 62 reviews
Home in Canaan
Private estate with Hot tub Tennis Court&Pool
May 18 – 25
$380 per night
4.71 out of 5 average rating, 52 reviews
Apartment in Lee
Lee time-share near ski hiking music
Mar 4 – 9
$195 per night
4.82 out of 5 average rating, 44 reviews
Guest favorite
Home in Sandisfield
Private gem in the Berkshires on the Buck River
Mar 16 – 23
$450 per night
4.96 out of 5 average rating, 24 reviews

Destinations to explore