
Family-friendly holiday rentals in Columbia County
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Top-rated family-friendly rentals in Columbia County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Cozy chalet w/ fireplace near Hudson & hiking
Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

Luxury Barn Retreat — All-Season Escape Awaits!
**Summertime access to nearby Queechy Lake beach!** An exceptionally private getaway on 8 beautiful acres near Chatham, NY, this historic barn has been meticulously renovated, including a full chef’s kitchen. It’s one of the area’s most stunning accommodations, ideally located between some of the most picturesque destinations— including the Berkshires, Great Barrington, Taconic State Park, Beebe State Forest, Ooms Conservation Area, Tanglewood, Hudson, Kinderhook, and so much more!

Hudson River Beach House
Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Hudson River Sunset Getaway
With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Boutique TINY home+private HOT TUB-walk to Main St
March-April midweek special: Bottle of prosecco, robes/slippers, s'mores. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful & private oasis, yet just a 2-min walk to Chatham’s Main St. lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis @artparkhomes.

Pond Side R & R
Our home is a close drive from Hudson, Kinderhook or Chatham, NY and a ten minute walk to the Hudson River and a boat launch. Enjoy miles of country roads for walking and biking and our nine acres through meadows and woods on mowed paths. Guests have access to an Adirondack style cottage overlooking a pond. Close to numerous restaurants, galleries, antique shops and cultural activities. This property is good for couples, a group of friends and families.

Chic Hudson Farmhouse w/ Fireplace & Porch
1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Peaceful Tiny House Escape by Hudson & Berkshires
Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Bright, Airy Home in Hudson w/ TONS of Character!
Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

The Ancram A - Luxury Mid-Century Modern Cabin
Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

Harmony Valley Home, bright & inviting studio
You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries & breweries Museums & art Hiking trails Empire State Rail Trail Conservation Areas Shopping
Popular amenities for Columbia County family-friendly rentals
Family-friendly home rentals with a hot tub

Modern and cozy 3 bedroom with outdoor oasis

Modern Home in Woods w/ Hot Tub 10 Miles to Skiing

Relaxing secluded stay with loving social animals.

Twin Island Lake House • Hot Tub

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Charming Lakefront Cabin with Hot Tub

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
Family- and pet-friendly home rentals

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Spacious Loft on Warren Street

Sugar Mountain Cabin: close to Hudson and nature

Scandinavian Cottage/Mountain Views/Fire pit

19th Century Mill House with River View

Private Hudson Valley Loft on 200 Acre Horse Farm

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Modern Upstate Cabin, near Rhinebeck NY
Family-friendly home rentals with a pool

Stunningly Designed Luxury Home w/ Pool & Hot Tub

Country Getaway Tiny House in woods w/Pool/Sauna

Catskill Mountain View Home with Hot Tub

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

Le Soleil Suite - Pool, Mtn Views Near Hudson

K House: Designer Home w Heated Salt Water Pool

Welcome to the Blue Cottage in Claverack NY
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- Hunter Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Saratoga Spa State Park
- June Farms
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Opus 40
- Berkshire Botanical Garden
- Walkway Over the Hudson State Historic Park
- Things to do Columbia County
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