Family-friendly holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

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.

17–24 Aug

$220 SGD per night

Guest favourite

Farm stay in Kinderhook

4.86 out of 5 average rating, 207 reviews

Barn House: isolated sheep farm Hudson area

April lambing season is not to be missed. A century-old brick barn, eclectic style with art everywhere, 10 miles from Hudson, near Kinderhook, now a quiet, secluded, unique residence. Gardens, sheep, and ponies are set off a country road, with a converted jungle shower, loft, and woodstove. Waterfall swimming area nearby. E-bikes are available to enjoy the nearby gorgeous Empire Trail. Easy drive to Columbia County and Berkshire spots. The farm shares space with nature as it is - country life.

11–18 Jul

$289 SGD per night

Guest favourite

Guest suite in Red Hook

4.9 out of 5 average rating, 300 reviews

the farmhouse suite at gallatin farmstead

A 575 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Of note, with a 30$ fee, we can set up a 2nd bed in the suite living room. We're happy to do it, it just takes some time to get together. It's a super comfortable mattress, the same model as the queen bed. We are also cycling happy and offer bike rentals and tours.

18–25 Jan

$225 SGD per night

Guest favourite

Home in Hudson

4.85 out of 5 average rating, 427 reviews

Pied-A-Terre | City of Hudson Entire Apartment

Entire Apartment in a gorgeous Queen Anne Victorian House located 2 blocks from Warren Street. Elegantly appointed with all the amenities one could need on their stay. Toasty warm. This is a sweet apartment located on the street level of my Queen Anne Victorian home. You have keyless access with your own front and back doors, access to the garden, laundry and all amenities. The apartment is cozy and full of charm and magic. * I am discouraging wedding party reservations during Covid*

11–18 Oct

$212 SGD per night

Guest favourite

Guest suite in Valatie

4.98 out of 5 average rating, 231 reviews

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!

1–8 Oct

$128 SGD per night

Guest favourite

Home in Ghent

4.9 out of 5 average rating, 258 reviews

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.

11–18 Sep

$317 SGD per night

Guest favourite

Home in Hudson

4.96 out of 5 average rating, 341 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

Complete renovation with privacy. Rural mill worker's cottage is upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a rural paved road and AHET Rail Trail. Minutes to Hudson and Kinderhook. You may see Carolina Wrens, Cardinals, Chickadees, Woodpeckers, Goldfinches and Hummingbirds. The creek to the front attracts Bald and Golden Eagles, Osprey, Blue Herons, Red Tail Hawks, Ducks and Geese. ABSOLUTELY NO PETS ALLOWED.

19–26 Feb

$256 SGD per night

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 482 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking.

3–10 Nov

$185 SGD per night

Guest favourite

Home in Copake

4.92 out of 5 average rating, 107 reviews

Copake Retreat

Our cozy 3 bedroom home is 120 miles from New York City and 150 miles from Boston. It's located in a friendly private lakeside community with 2 sandy beaches on Robinson Pond. The surrounding area is gorgeous with rolling hills and farms. We're within a half-hour drive from Great Barrington, MA., Hudson, NY, and Millerton, NY. and it's a very short drive to Taconic State Park. Enjoy our 4-season Copake Retreat!

12–19 Jul

$228 SGD per night

Guest favourite

Cottage in Copake Falls

4.91 out of 5 average rating, 320 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

14–21 Dec

$222 SGD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 306 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

22–29 Aug

$631 SGD per night

Guest favourite

Guest suite in Nassau

5.0 out of 5 average rating, 225 reviews

Country Two Bedroom Apartment with full breakfast

A ground floor, two bedroom apartment in host's house. Full breakfast provided. Located in New York's scenic Hudson Valley and convenient to Hudson, the Berkshires, the Catskills, Saratoga, Albany, and more. Full kitchen, separate dining room, private covered patio. Access to 23 acres of open and wooded property.

17–24 Jan

$183 SGD per night