House holiday rentals in Kingston

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

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.

Historic 1800s Kingston Waterfront Townhouse

Welcome to our newly renovated two story home in beautiful scenic Kingston, NY. This 3 bedroom, 2 bath loft style home is perfect for many occasions! It boasts a full kitchen stocked with modern stainless steel appliances and style for days. Marvel at the open Brooklyn loft style designing that will impress with its exposed brick and white wood ceiling rafters and light gray floors. Very chic! It is fully furnished with posh sofas and tables that lend beautifully to the sophisticated ambience.

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.

Uptown kid & dog friendly home w/fireplace & yard

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.

Peaceful Retreat in the Heart of Kingston

The Winchell is a thoughtfully designed space in the heart of Kingston, with 2 bedrooms, and 1 bath. The home, the oldest on the block with many original details preserved, is located in a quaint & quiet part of Midtown (the Arts district), ¼ to 2 miles away from the local restaurants, cafes, shops, and bars that's made Kingston a prime Hudson Valley destination. It is also a hub to nearby trails, outdoor adventures, and towns such as Rhinebeck, Phoenicia & Woodstock. Licensed STR: 004980

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Historical Walkable Stockade Retreat • c.1811

Capture a slice of Kingston's heritage in this historical frame home, built in 1811 by the sheriff for his daughter. Thoughtfully updated, the house retains beautiful period details like double-hung windows, Federal-style staircase, and decorative fireplaces—all paired with comfortable, contemporary furnishings. Family-friendly amenities make it a great spot for travelers of all ages. A charming house filled with character and history for you to enjoy—just be patient with her quirks!

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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...

Cozy Winter Upstate Cabin

Beautiful 2 bedroom/1 bath home centrally located between Woodstock and Saugerties in the gorgeous Catskill Mountains. Come for hiking, skiing, shopping and dining, it is all at your fingertips! Your home is a chic cabin situated on a large property and provides a fully stocked kitchen if you choose to cook at home, a gas grill, and fire pit in the back yard for evening enjoyment. Visit the many fun shops just down the road, or one of our lovely locally owned restaurants! Enjoy!