Family-friendly vacation rentals in Columbia County

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.

Leeds Escape

DISINFECTED FOR COVID-19 after each visit... Newly updated guest house attached to main house. Entrance is in the back. Read a book, relax or take in nature. From enjoying cows and Horses, to goats next door and the chirping of the birds. Fire 🔥 pit night. BBQ or simply stay in doors cooking. Take a stroll to Catskill Creek. Or take 3 Minute drive to town...for breakfast, lunch or dinner. Hunter Mountain Skiing 35 minutes away. Windham Mountain Skiing 26 minutes. Kaaterskill Falls 26 minutes.

Hudson Arts

Luxury Hudson Rental, in a Unique Historical Facility! Perfect for first time visitors. Among the city's largest Private, Open-Plan Homes. Possible to accommodate VIPs & Celebrities. Loft-Style layout hearkens to Soho living. Restaurant-scale kitchen is helpful for entertaining. Historic preservation adds to the experience, while "Flex Space" allows for multiple configurations: Dinners, Private Parties, etc. A rare experience, in a most unique Hudson facility. (Update: A/C being upgraded 2024)

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

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.

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

320 State - Beautiful Backyard 2 blks from Warren

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. This is a 900 sqare foot apartment filled with light. You have keyless access with your own front and back doors, parking in the back, access to the garden, laundry and all amenities. The apartment is cozy and full of charm and magic.

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.