Family-friendly vacation rentals in Columbia County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Columbia County

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

Guest favourite
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. 3 – 10
$272 CAD per night
4.99 out of 5 average rating, 293 reviews
Guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!
May 15 – 22
$134 CAD per night
4.98 out of 5 average rating, 229 reviews
Superhost
Home in Ghent
Renovated guesthouse on 52 acres!
Come and stay in our beautiful guesthouse in Ghent, upstate NY. Relax and rejuvenate. Hike our private trail in the woods, grill up some food, and chill with a book by the pond... Enjoy the countryside! Go explore cute towns such as Hudson, Chatham and Great Barrington. PLEASE NOTE: My husband and I are both fully vaccinated for Covid-19. And so is our cleaning lady and our caretaker. Please know that we are taking the actions we can, to disinfect the guesthouse in between guests.
Oct. 11 – 18
$331 CAD per night
4.9 out of 5 average rating, 255 reviews

Popular amenities for Columbia County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Craryville
The City Farmers Upstate. Farm house with hot tub
Sep. 29 – Oct. 6
$568 CAD per night
4.93 out of 5 average rating, 216 reviews
Guest favourite
Home in Craryville
Modern Home in Woods | Hot Tub | 20 mins to Skiing
May 12 – 19
$539 CAD per night
4.98 out of 5 average rating, 182 reviews
Guest favourite
Home in Hudson
Livingston Farmhouse Escape with hot tub and sauna
Apr. 8 – 15
$765 CAD per night
4.95 out of 5 average rating, 245 reviews
Guest favourite
Home in Hudson
Hudson Country Cottage, Fireplace, Pond, Hot Tub
Feb. 8 – 15
$557 CAD per night
4.84 out of 5 average rating, 220 reviews
Guest favourite
Home in Ancramdale
Ski & unwind in the country, stargaze in hot tub
Mar. 12 – 19
$294 CAD per night
4.93 out of 5 average rating, 126 reviews
Guest favourite
Home in Red Hook
Wooded Retreat w/ Hot Tub and Trout River
Sep. 26 – Oct. 3
$413 CAD per night
4.88 out of 5 average rating, 212 reviews
Guest favourite
Townhouse in Hudson
Palazzo Hudson: The Luxury Spa Retreat
Feb. 2 – 9
$1,274 CAD per night
4.94 out of 5 average rating, 189 reviews
Guest favourite
Home in Ghent
Luxe Retreat+Sauna+HotTub & Swimming on 12 acres
Aug. 16 – 23
$1,441 CAD per night
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Hudson
Secluded Hudson mid-century - pool & hot tub
Jun. 9 – 16
$1,151 CAD per night
4.97 out of 5 average rating, 59 reviews
Guest favourite
Home in Elizaville
Peaceful Hudson Valley Retreat House with HOT TUB!
Jan. 21 – 28
$472 CAD per night
4.84 out of 5 average rating, 87 reviews
Superhost
Home in Hudson
Cozy Chic Home, Hot Tub, Near Warren St
Jan. 26 – Feb. 2
$733 CAD per night
4.76 out of 5 average rating, 183 reviews
Guest favourite
Home in East Chatham
Hot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Jul. 22 – 29
$411 CAD per night
4.79 out of 5 average rating, 167 reviews

Family- and pet-friendly home rentals

Guest favourite
Cottage in Red Hook
bright serene + spacious barn
Jul. 31 – Aug. 7
$467 CAD per night
4.98 out of 5 average rating, 586 reviews
Guest favourite
Farm stay in Kinderhook
Barn House: isolated sheep farm Hudson area
May 5 – 12
$270 CAD per night
4.85 out of 5 average rating, 198 reviews
Guest favourite
Cabin in Hillsdale
Tory Hill Cabin; (North Mountain Cottages)
Jul. 20 – 27
$257 CAD per night
4.9 out of 5 average rating, 168 reviews
Guest favourite
Home in Athens
Athens/Catskill/Hudson Victorian Cottage
Aug. 12 – 19
$224 CAD per night
4.78 out of 5 average rating, 217 reviews
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home.
Jan. 30 – Feb. 6
$508 CAD per night
4.93 out of 5 average rating, 187 reviews
Guest favourite
Guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
Apr. 3 – 10
$234 CAD per night
4.93 out of 5 average rating, 166 reviews
Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Aug. 16 – 23
$799 CAD per night
4.81 out of 5 average rating, 243 reviews
Guest favourite
Cottage in Ancram
Warmer Temps & Special Rates-Now Is the Time To Go
Feb. 4 – 11
$322 CAD per night
4.99 out of 5 average rating, 165 reviews
Guest favourite
Home in Great Barrington
Your own private Berkshires retreat
Nov. 17 – 24
$491 CAD per night
4.9 out of 5 average rating, 111 reviews
Guest favourite
Yurt in Germantown
Stargazer Upstate glamping at Gatherwild Ranch
May 12 – 19
$332 CAD per night
4.92 out of 5 average rating, 195 reviews
Guest favourite
Cabin in Hillsdale
Rustic, peaceful and affordable cabin
Apr. 27 – May 4
$280 CAD per night
4.8 out of 5 average rating, 301 reviews
Superhost
Apartment in Hudson
3 blocks to Warren ST with back yard and BBQ fa
May 8 – 15
$202 CAD per night
4.86 out of 5 average rating, 123 reviews

Family-friendly home rentals with a pool

Guest favourite
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
Aug. 14 – 21
$683 CAD per night
4.96 out of 5 average rating, 300 reviews
Guest favourite
Home in Sheffield
Race Mountain House
Jul. 25 – Aug. 1
$871 CAD per night
4.85 out of 5 average rating, 114 reviews
Guest favourite
Villa in Catskill
WILDINGS on Hudson - River Estate w amazing views
Nov. 20 – 27
$1,281 CAD per night
4.97 out of 5 average rating, 67 reviews
Guest favourite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Nov. 4 – 11
$1,697 CAD per night
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Dec. 16 – 23
$1,161 CAD per night
4.99 out of 5 average rating, 68 reviews
Superhost
Home in Barrytown
Gorgeous 4 BR-4BR House and Pool/ Unique Location
Oct. 7 – 14
$477 CAD per night
4.84 out of 5 average rating, 19 reviews
Guest favourite
Home in Old Chatham
Samuel Wilbur Estate since 1810
Apr. 11 – 18
$1,225 CAD per night
4.96 out of 5 average rating, 27 reviews
Superhost
Home in Catskill
House with pond,pool, very relaxing retreat
Jan. 9 – 16
$597 CAD per night
4.68 out of 5 average rating, 103 reviews
Superhost
Home in Hillsdale
Historic JP Dorr House near Catamount Hillsdale NY
Jun. 23 – 30
$519 CAD per night
4.58 out of 5 average rating, 43 reviews
Superhost
Home in Hudson
Hudson Farmhouse w/ pool & Catskill mtn views
Jul. 19 – 26
$1,280 CAD per night
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in Hillsdale
Charming 1800 Eyebrow Colonial
Jan. 19 – 26
$405 CAD per night
4.75 out of 5 average rating, 28 reviews
Guest favourite
Home in Ghent
Low Meadow Farm - Hudson Valley, NY
Sep. 9 – 16
$1,205 CAD per night
5.0 out of 5 average rating, 46 reviews

Destinations to explore