Holiday rentals with outdoor seating in Kingston

The Ivy on the Stone

The oldest house you can stay at in the historic heart of Kingston! Walkable! This landmark 1680 stone house has been featured in Upstate Diary and Houzz. Enter this 350 sq ft luxe apartment through a secret garden and a shared porch. The private spa-like bathroom features a clawfoot tub, and rain shower. Featuring an organic queen bed, an electric fireplace, workspace, William Morris wallpaper, and a Nespresso maker. If you want to stay in the larger house visit: https://abnb.me/EexspArCAIb

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.

Luxury A-Frame Cabin in the Woods with Sauna

Modern, glass‑fronted A‑frame perched in the Catskills, offering sweeping mountain vistas. Relax in the private cedar barrel hot sauna & refreshing outdoor shower, gather round the smokeless propane fire-table, or fire up the propane grill for al‑fresco dinners. A stylish bedroom with woodland views, luxe linens, fast Wi‑Fi, and a cozy electric fireplace blend comfort with design. Minutes to trailheads, waterfalls & farmers markets - ideal for couples seeking a serene and restorative escape.

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 freshly 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.

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.

Chic, Private Cabin with Stunning River Views

Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.

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...

Dog Friendly Uptown Apt Near Stockade + Backyard

2 hours from NYC, escape to this pet-friendly outdoor oasis in Uptown Kingston only a short walk from the Historic Stockade District. Renovated in 2020, this 1-bedroom apartment is accented with vintage decor, indoor plants and has a huge backyard for your pup. Use the full kitchen or walk to the many restaurants in the Stockade. The expansive backyard includes a stone patio, outdoor table for dining, Adirondack chairs & hammock. Free driveway parking, WIFI, and Netflix!

Woodland Neighborhood Retreat

Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.

Fresh & Charming Private Uptown Apartment

Welcome to our inviting and light 2-bedroom apartment in uptown Kingston. The location is a walker's paradise with the best of the historic Stockade district just a stroll away, and is well-situated to explore the Hudson Valley and the Catskill Mountains. Comforts include a leather sectional sofa, Roku SmartTV, HD projector, dishwasher, deluxe bedding for a dreamy night's sleep, blackout curtains, a sound machine, and two armchairs on the front porch.

Swan Cottage with Expansive Hudson River Views

The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.