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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
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Cabin in Monterey
4.95 out of 5 average rating, 258 reviewsAmazing Berkshire Mountains Cabin
![](https://a0.muscache.com/im/pictures/miso/Hosting-25647014/original/072b90f8-da81-45c7-ab99-cfefb09a426f.jpeg?im_w=720)
Home in East Chatham
4.79 out of 5 average rating, 177 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
![](https://a0.muscache.com/im/pictures/877866b4-8265-452f-9f3c-89424946d040.jpg?im_w=720)
Home in Pittsfield
4.8 out of 5 average rating, 169 reviewsBeautiful House By The Lake W/Jetted Hot Tub
![](https://a0.muscache.com/im/pictures/90824439-b517-4318-bd37-399b6932c144.jpg?im_w=720)
Cottage in Becket
4.63 out of 5 average rating, 155 reviewsA Magical Spot on Little Robin Lake
![](https://a0.muscache.com/im/pictures/178a71c4-cc7e-4e23-8398-2fae527d83e0.jpg?im_w=720)
Home in Lee
4.96 out of 5 average rating, 77 reviewsSpectacular Berkshire Retreat on Private Lake
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Chalet in Richmond
4.97 out of 5 average rating, 90 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
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Home in Lee
4.69 out of 5 average rating, 87 reviewsRANCH at FOX HOLLOW on Laurel Lake
![](https://a0.muscache.com/im/pictures/20a376b3-3005-4a84-8459-4244167b45fa.jpg?im_w=720)
Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin
Family- and pet-friendly home rentals
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Cottage in Lanesborough
4.84 out of 5 average rating, 263 reviewsWildlife Lakeside Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-1437957/original/b3c876b5-6b24-409f-ac9d-fe9ee58b1c9f.jpeg?im_w=720)
Rental unit in Sandisfield
4.92 out of 5 average rating, 232 reviewsSunny Berkshire Studio Apartment
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Home in Dalton
4.93 out of 5 average rating, 176 reviewsBrooksong, the perfect Berkshires getaway
![](https://a0.muscache.com/im/pictures/cdf98798-dae6-4ff7-b79c-e9b351731e19.jpg?im_w=720)
Cabin in Lee
4.91 out of 5 average rating, 109 reviewsCabin with views in the Berkshires!
![](https://a0.muscache.com/im/pictures/230afd9d-b153-48f2-81a8-e100415dcca3.jpg?im_w=720)
Farm stay in New Ashford
4.9 out of 5 average rating, 228 reviewsSheep Barn on the Greylock Valley Estate
![](https://a0.muscache.com/im/pictures/miso/Hosting-78385/original/8f9862ec-5e43-4f54-bbc9-66499026583d.jpeg?im_w=720)
Home in Cheshire
4.85 out of 5 average rating, 206 reviews19th c. Barn in The Berkshires
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Home in Great Barrington
4.9 out of 5 average rating, 114 reviewsYour own private Berkshires retreat
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Home in West Stockbridge
4.86 out of 5 average rating, 105 reviewsPeaceful Stockbridge Cabin in the Woods
Family-friendly home rentals with a pool
![](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
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Bungalow in Williamstown
4.88 out of 5 average rating, 205 reviewsHollywood Bungalow in the Berkshires
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Home in Great Barrington
4.97 out of 5 average rating, 37 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
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Home in Pittsfield
4.98 out of 5 average rating, 42 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
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Home in Canaan
4.99 out of 5 average rating, 76 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
![](https://a0.muscache.com/im/pictures/40071198/9a97c8dc_original.jpg?im_w=720)
Home in Sheffield
4.82 out of 5 average rating, 115 reviewsRace Mountain House
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Home in Hancock
4.86 out of 5 average rating, 43 reviewsJiminy Peak Peaceful Home in Berkshires
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MjMzMTg2NzY%3D/original/f825bf36-6eb1-4b73-a1b2-976ae31a0407.jpeg?im_w=720)
Home in Canaan
4.71 out of 5 average rating, 56 reviewsPrivate estate with Hot Tub, Tennis Court & Pool
Destinations to explore
- Family-friendly rentals United States
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- Family-friendly rentals Massachusetts
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- Yurt Rentals United States
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