House holiday rentals in Kingston

Large 2-BR apartment in historic waterfront home

This sophisticated, cozy, pet-friendly historic home in Kingston's beautiful, walkable downtown waterfront (Rondout National historic district) is close to restaurants, sidewalk cafes, boutiques, parks, a beach, museums, galleries, and more. It features a beautiful front porch and back deck, fenced-in yard, living room, master bedroom (queen bed), 2nd bedroom with (full-sized bed), and den/study adjacent to the second bedroom. It is the perfect retreat for a couple, friends, or a small family.

Location · Family · Nearby

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Family · Value · Access

Uptown kid/dog friendly home w yard tennis & park

Sunny Colonial Uptown Across from Park | Dog-Friendly | Family-Ready Bright, airy, and perfect for exploring Kingston and the Hudson Valley. This home is designed for comfort, fun, and relaxation. Step outside and you’re across from park with trails, playground, petting zoo, tennis courts, and a dog park—something for everyone. Whether you’re planning a family or romantic getaway, weekend with friends, or a pet-friendly escape, this home has every comfort and a prime and walkable location.

Value · Family · Parking

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

Welcome friends to our beloved waterfront cottage right on the Esopus Creek, in the beautiful Catskills! Whether you’re seeking a peaceful retreat, fun for the family, or a romantic escape, our 2-bedroom home is your perfect Catskills destination. With kayaks for adventures on the creek (Spring through Fall), a firepit with water views, outdoor dining with a grill, and located close to lots hiking and nearby towns, like Woodstock and Saugerties, you'll only wish you could stay here longer!

Family · Value · Long stay

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.

Value · Family · Nearby

Antique Uptown Charmer w/ Five-Star Modern Kitchen

The best of modern designed paired with authentic historic Kingston bones. The house features 3 full luxe baths, HUGE new chef's kitchen with endless work surfaces - 3 ovens, and baking equipment galore. 2 full floors (+basement) offer room to cook and play, flowing from the kitchen to the dining deck to the hot tub deck. This restored home will be your base camp for adventures, but once you come you won’t want to leave! Quiet workspaces, printer, choose your vibe to get work done.

Location · Value · TV

Rhinecliff on the Hudson

Welcome to our home, Rhinecliff on the Hudson. Our home located in Rhinecliff, 3-4 mins to Rhinebeck Village. Sleeps 8 total. 1st Floor: King Bedroom, Queen Bedroom 2nd Floor: Living Room and Kitchen 3rd Floor: Loft with 2 Queen Beds, Living Room, Office Amazing views of the Hudson River + steps from the train station. Home is spacious with high ceilings, incredible wood work, and outdoor deck with couch, table, chairs, and umbrella. You'll love the view and convenient location.

Value · Location · Check-in

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Location · Family · Nearby

Hudson River View w/ Hot Tub & Sauna near Kingston

Water views of the Hudson River from this 3 story wellness chalet style home with plenty of outdoor space. The home offers an outdoorsy feel for relaxing just outside downtown Kingston (car is needed, 5 minutes). Perfect for summer or winter and working from "Home". The home includes a sauna, hot tub, fenced backyard for your pet, 3 decks (the second-story deck is covered so if there's a thunderstorm you can still relax and enjoy the outdoors), grill, and a gas fire pit.

Value · Location · Sleep quality

Modern Escape • Sauna • Firepit • Near Woodstock

Perfect upstate escape! Whether you're planning a romantic couples getaway, a fun trip with friends, a family vacation, or even a much-needed solo escape, The Retro Chic House offers the ideal stay for a memorable local Upstate Experience. This stunning renovated property is designed to cater to a variety of preferences and is guaranteed to provide you with an unforgettable stay. Located 8 mins to Woodstock, 12 mins to Saugerties, & picturesque drive to Hunter!

Value · Location · Amenities

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

Location · Value · Condition

Charming Historic Home Near Waterfront Restaurants

The best of both worlds: our 1870s house fits right into its historic Rondout neighborhood, but with funky modern design, style, comfort and amenities. Relax in a beautiful zen-like outdoor oasis with pond and dining and lounging areas. Walk just a few blocks down to the waterfront where you’ll find cafes, restaurants, antique stores, boutiques, and museums; grab a freshly fried donut and coffee, and watch the boats go by from a bench in the park.

Location · Value · Bathroom