Family-friendly vacation rentals in Kingston

Colonel Hasbrouck’s 1735 Stone House, Street Level

Step through the red door into a designated landmark dating from 1735. Light from tall colonial Dutch windows reflects off the hand-restored wide-board floors and the decorative fireplace. There’s a backyard view through the split Dutch door. The apartment is cleaned according to Airbnb's enhanced cleaning protocol. It has a small Roku TV, and an infant pack and play, high chair, and bouncer seat. Internet is powered by the fastest tier available. Downstairs you'll find a bright and airy living room in the front, the light from the tall colonial dutch windows reflected off of the hand-restored original wide-board floors. Past the large decorative fireplace is a newly renovated full kitchen and dining nook, with a backyard view through the split dutch door. Upstairs is a modest but modern bathroom with a heated towel rack, and two bedrooms, each with a 12" queen-sized memory foam mattress on a solid steel frame. For your comfort, the apartment has its own heating and cooling controls, with separate programmable thermostats for upstairs and downstairs. Check-in is done automatically via keypad (your personal code is sent via email when you book), but we’re right next door to answer your questions or point you to a good restaurant. The Colonel Abraham Hasbrouck House is in the historical Stockade district. At the center of Kingston, the first capital of New York State, the neighborhood is charming and walkable with some great restaurants, bars, cafes, and shops. Here's how most folks get here. By bus: 5 minutes on foot from the Trailways bus terminal, about 2 hours from the Port Authority By car: 3 minutes from exit 19 of I-87, about a 90-minute drive from the GW bridge. By train: 20 minutes by car from the Rhinecliff Amtrak station, about 2 hours by train from Penn Station If you're coming by car, parking is free on our street, and finding a spot is usually pretty easy on weekends and weekdays after 5pm. Otherwise, there are 3 paid municipal lots you can use, all within two blocks. We've taken a lot of care to preserve the original wide-board floors, but since they came from trees that started growing before Henry Hudson came up the river, they're crooked and creaky. Take care when walking on them and the stairs to the bedrooms upstairs, and feel free to use the slippers we've provided.

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.

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.

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!

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...

Lovely 1 bedroom apt. with free parking in Rondout

Large 1 bedroom apartment with 10 foot ceilings, located in Kingston Historic Rondout District. Queen size bed and one large futon conversation, there are large pocket doors that separate the bedroom from the living room, pool table, lots of natural light, blackout curtains , air conditioning, claw foot tub, small private patio, 60 inch wall tv, walk to the historic Rondout water front, restaurants, boat rides, trolly, art galleries, Kingston Point Beach and Hudson Brickyards.

Renovated apartment in midtown Kingston

Our renovated Kingston apartment. House was built in 1888 and has been lovingly renewed and restored. We fussed over every detail and tried to make the space as comfortable and inviting as we could. Many of the furniture pieces we made, or restored. We refinished the old floors and completed re jigged the layout for a more open plan, connected living space. Kitchen and bathroom are completely brand new! The house is in the middle of everything Kingston, and the HV has to offer.

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 koi pond, seasonal stream feature, 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.

Spacious, Bright & Airy! Tangerine Dream Suite

You will enjoy easy access to everything from this centrally located apartment. Your right next door to Ulster Performing Arts Center & Tubbys where you will find amazing shows and live music! West Kill Brewing is walking distance as well as many restaurants and coffee shops. Downtown Hudson River waterfront packed with restaurants and water views is a 5 minute drive. Grab a pair of skates and go ice skating at The Rondout Rink right on the waterfront.

Gorgeous and Expansive Uptown Kingston Loft

Located in historic Uptown Kingston, this space is conveniently located and exceptionally spacious. This two floor loft space is spread across 1600 square feet with rustic hardwood floors, two queen beds on separate floors, a full bath, kitchen, dining table and living spaces on each floor. Walkable to grocery, coffee, take out, park, bicycle rental, liquor store, all the essentials! Kingston STR License No. 016240.

Guest Apartment in Converted 1870s Carriage House

Pine Place is a sunny, private retreat set in a historic residence. The space feels warm and welcoming, with neutral earth tones, soft whites, and an open, airy lounge area that invites you to settle in and unwind. The fully equipped kitchen makes longer stays a breeze, and just outside, a front patio with a breakfast nook is the perfect spot to start your morning.