Pet-friendly holiday rentals in Columbia County

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

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.

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Private Hudson Valley Loft on 200 Acre Horse Farm

Escape to Germantown, explore the farm’s 200-acres and visit the horses. they love carrots and visitors! Bright and airy open floor plan loft in Germantown, NY. Once an apple storage barn, this recently remodeled loft features two bedrooms, each with its own private bathroom, beautiful original pine floors, gas fireplace, central air, cook’s kitchen, and a large outdoor deck overlooking open fields and a pond. We are dog friendly up to 2 dogs. There is a $50.00 fee per dog. NO CATS.

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Renovated historic home, walk to Hudson River!

Escape from the city and enjoy slowing down in upstate New York in this bright and spacious historic home! Just a short walk to the historic Town of Athens and the Hudson River where you can sit by the water, enjoy a picnic, or kayak/canoe. This home is made for cozy unwinding and is stocked with everything you need to cook a wonderful meal (cast irons, French cookware, baking supplies, spices and oils). 1 king bed with view of the river, 1 queen bed + a full air mattress available.

Artist's Studio, Catskills Views

Top rated large studio with gorgeous light and Catskill Mountain Sunsets. Formally an artist studio, the space features a luxurious bathroom with a glass walled shower. The modern well equipped kitchen has a full sized refrigerator, microwave, toaster, cooktop, outdoor grill Private deck for outdoor lounging and dining Set on a private park like 65 acres, directly on the Hudson River with walking trails Germantown 5 minutes. 10 minutes to Tivoli, Hudson or Bard College.

bright serene + spacious barn @barn and bike

a bright serene space built by us on the property we live on. we are in - what we think - is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes all around. 6 quaint towns are within 10-25 minutes drive. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

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.

Farm Cottage w/ Donkeys, Fire Pit & Wood Stove

Welcome to The Cottage at Raspberry Ridge, a charming Hudson Valley farm stay surrounded by gardens, woodlands, donkeys, and chickens. This cozy 3-bedroom retreat blends rustic character with modern comfort, offering a wood-burning stove, peaceful outdoor spaces, and access to the farm grounds. Just minutes from Hudson, Great Barrington, hiking trails, and local farms, it's the perfect place to slow down and reconnect.

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub + She-Shed. Escape to this 300 sq ft tiny home with private hot tub. A peaceful, romantic getaway in the heart of Chatham—just steps from dining/drinks, shops/theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat @artparkhomes.

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake