
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.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Rustic Secluded Cabin near Berkshires. *wood stove
The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

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!

Cheerful 3-bedroom cottage with woodstove.
Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

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 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!

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.

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

Escape to Lakefront Leisure—Amazing views!

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

Relaxing secluded stay with loving social animals.

Twin Island Lake House • Hot Tub

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

Tivoli Star Gazing Cabin

Sugar Mountain Cabin: close to Hudson and nature

Scandinavian Cottage/Mountain Views/Fire pit

Private Hudson Valley Loft on 200 Acre Horse Farm

Modern Barn on 12 acres w Sauna, FirePit+swimming

Patchin Mills Quaint Country Cottage

Sackett & Van Dam Guest House @ Little 9 Farm 1706
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

K House: Designer Home w Heated Salt Water Pool

Welcome to the Blue Cottage in Claverack NY

Secluded classic farmhouse near Hudson-pool+hottub
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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
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