Family-friendly vacation 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.
Vacation 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
Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
Home in Pittsfield
4.81 out of 5 average rating, 171 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Home in East Chatham
4.79 out of 5 average rating, 184 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Rental unit in Lee
4.92 out of 5 average rating, 25 reviewsDream Vacation
Home in Lee
4.96 out of 5 average rating, 77 reviewsSpectacular Berkshire Retreat on Private Lake
Cabin in Becket
5 out of 5 average rating, 265 reviewsWaldtreff - quiet grand cabin
Home in Lanesboro
4.95 out of 5 average rating, 19 reviewsMy Mountain Haven- The Perfect Escape
Family- and pet-friendly home rentals
Home in Lanesborough
4.9 out of 5 average rating, 108 reviewsElmwood Farmhouse
Farm stay in New Ashford
4.89 out of 5 average rating, 238 reviewsSheep Barn on the Greylock Valley Estate
Home in Otis
4.94 out of 5 average rating, 142 reviewsBerkshires hideaway! Hikes & serenity near lake
Home in Williamstown
4.82 out of 5 average rating, 187 reviewsWalking distance to downtown
Rental unit in Sandisfield
4.92 out of 5 average rating, 235 reviewsSunny Berkshire Studio Apartment
Cottage in East Chatham
4.93 out of 5 average rating, 202 reviewsBeautifully Nestled Berkshires Home
Cabin in Hillsdale
4.8 out of 5 average rating, 314 reviewsRustic, peaceful and affordable cabin
Cabin in Lee
4.91 out of 5 average rating, 117 reviewsCozy winter escape at The Beaver Dam!
Family-friendly home rentals with a pool
Home in Hancock
4.86 out of 5 average rating, 44 reviewsJiminy Peak Peaceful Home in Berkshires
Home in Pittsfield
4.98 out of 5 average rating, 50 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Great Barrington
4.88 out of 5 average rating, 17 reviewsFun Farmhouse
Home in Great Barrington
4.93 out of 5 average rating, 46 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
Home in Canaan
4.99 out of 5 average rating, 83 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Condo in Hancock
4.85 out of 5 average rating, 142 reviewsCozy Condo @ Jiminy Peak
Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
Home in Canaan
4.67 out of 5 average rating, 63 reviewsR3Bliss - Estate with Hot Tub, Tennis Court & Pool
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with breakfast Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with a patio Berkshire County
- Hotel rentals Berkshire County
- Rentals with beach access Berkshire County
- Beachfront rentals Berkshire County
- Monthly Rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Rentals with a kayak Berkshire County
- Private suite rentals Berkshire County
- Rentals with pools Berkshire County
- House rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with lake access Berkshire County
- Bed and breakfasts Berkshire County
- Boutique hotel rentals Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with a washer and dryer Berkshire County
- Farmstay rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Cottage rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Chalet rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Guesthouse rentals Berkshire County
- Rentals with a sauna Berkshire County
- Waterfront 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
- Things to do United States
- Food and drink United States
- Wellness United States
- Sports activities United States
- Nature and outdoors United States
- Entertainment United States
- Sightseeing United States
- Art and culture United States
- Things to do Massachusetts
- Art and culture Massachusetts
- Food and drink Massachusetts
- Sightseeing Massachusetts
- Nature and outdoors Massachusetts
- Things to do Berkshire County