Family-friendly holiday rentals in Columbia County

Design-Forward Riverfront Cabin on 120 Acres

Far from the road, a tranquil modern cabin sits directly above a state-stocked fly-fishing and tubing river - an intimate, private escape under two hours from NYC. Set on a 120-acre property, with access to trails, river swimming, and a private cabin beach, you’ll feel completely secluded while still being 10–30 minutes from Red Hook, Rhinebeck, Hudson, and Kingston. Radiant floors, a Swedish composting toilet, Tesla Powered, w/ 500 Mbps fiber internet make it easy to unplug without sacrificing.

Cozy Grove Luxury Cabin

Luxurious, lovingly-appointed mid-century country retreat located less than 15 minutes from restaurants, galleries, and shopping in downtown Hudson, nestled between farmers’ markets, breweries, cideries, distilleries, hiking, and more! Recently-renovated 1958 cabin features a deep soaking tub, outdoor hot tub, woodstove, and upscale amenities. Set back from the road amidst a grove of pine and apple trees, it's the perfect spot for kicking back in luxury after a day exploring local attractions.

Welcome to Casa Bartolo, Your Oasis on the Hudson!

It's now wildflowers season! Why book a hotel when you can enjoy a charming, private 2-bedroom suite with breathtaking views of the Catskill Mountains, Hudson River, and stunning sunset! This tranquil retreat offers: Private Entrance, Private shared Bathroom, Kitchenette, cedar soaking tub & easy parking. Wake up to the sunrise and enjoy a cup of Nespresso or tea. Whether you want to relax, walk, jog, bike, meditate, smell the lilacs & pick eggs or simply unwind, this is the perfect escape.

Secluded Magic Treehouse Escape

Poetic. Unique. Romantic. 25ft high. The sounds, smells, and fresh air of nature are all yours. 10mins to town. Surrounded by old oaks, maples, and pine trees. Details abound. Simple and minimal yet elegant. Rustic Luxe. Windows all around bring in nature, screens keep it outside. All the modern conveniences, and then some. Hot and cold running water, equipped kitchen, full bath, 2 bedrooms with queen beds, nice linens and details, plus outside shower, 2 decks, BBQ, fast WIFI, TV, etc.

Livingston Farmhouse Escape with hot tub and sauna

Perfect country getaway conveniently located near Hudson, Red Hook, Tivoli and Germantown; in the heart of a sweet hamlet. Farm stands and swimming holes abound! Our home is an open and airy 3 bedrooms; space to spread out, and a large kitchen equipped with all a cook could want. Generous living room with cozy fireplace and Roku TV. Sonos throughout first floor. Huge property with fire pit for s'mores and late night fun; grill, patio dining, sauna and hot tub. Extensively renovated in 2026.

Quiet• pvt farmhouse•stunning mntn views nr Hudson

This welcoming and private 4-bedroom, 2.5-bath farmhouse is a sight to behold. Spacious and sun-drenched, with large windows, exposed beams and an open floor plan, this home looks out over a view from Bear Mountain through the Catskills with stunning sunsets. Here is a blissful sanctuary to relax and recharge, atop a hill on 8 private acres, yet in less than 15 minutes you can be shopping or dining in Hudson. Two stories of space and comfort-- you will want to return!

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.

Boutique TINY home+private HOT TUB-walk to Main St

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

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.

Riverside Retreat on the Hudson - Modern Cottage

Welcome to the Riverside Retreat on the Hudson, a modern renovated cottage located directly on the Hudson River! Enjoy the beautiful panoramic views from the comfort of the house or in the Adirondack chairs on the patio. Secluded and serene, yet minutes away from downtown Catskill (5 minutes) and Hudson (15 minutes). Hunter and Windham are 30 minutes away for hiking and skiing! We are so excited to share this very special place with you!

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.