Family-friendly holiday rentals in Kingston

5 out of 5 average rating, 104 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.

4.97 out of 5 average rating, 344 reviews

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

4.87 out of 5 average rating, 111 reviews

A cleanly designed space features a light wooden floor, leading into a bright bedroom with a spacious bed framed by soft gray linens. Natural light filters through sheer curtains, illuminating a minimalist chair and a stylish lamp in the foreground.

Flat in Port Ewen

Near-Kingston Staycation Home

This is a newly renovated home in a two-unit house in Port Ewen, 5 min to historic Kingston. We have carefully planned and renovated this home with a work/leisure lifestyle in mind. The space is designed for an individual, a couple, close friends, or a small young family. There are swimming places and parks walking distance as well as amazing coffee, shopping, art, attractions, events, etc. Note that this place has noise from traffic on the main road (ear buds and white noise machine provided).

4.95 out of 5 average rating, 239 reviews

A cozy living space features a stylish leather couch and a flat-screen TV. A wooden barn door leads to the adjoining bedroom, while natural light enters through two windows adorned with simple coverings. A plant adds a touch of greenery, enhancing the atmosphere.

Guest house in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

The historical frame house showcases a charming exterior with a blue wooden facade, surrounded by snow-covered trees. A winding road leads to the entrance, while decorative lampposts and a nearby yellow house frame the scene, creating a peaceful winter atmosphere.

4.98 out of 5 average rating, 175 reviews

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!

The open living area features tall windows that provide ample natural light. A comfortable sofa is situated beside a wooden coffee table, with a dining table set for four in the background. Modern appliances and a stylish ventilation hood enhance the kitchen space.

4.97 out of 5 average rating, 153 reviews

DeMew Place

Enjoy the historic Rondout district of Kingston while relaxing in this beautiful, one-bedroom, one bath unit on the first floor of a brick building from 1900. Historic charm meets modern amenities, with 12' ceilings, in-floor heating, and an open concept kitchen, living and dining area across the street from the Hideaway Marina on the Rondout Creek. Take a relaxing walk along the water to the historic waterfront area on Broadway for dining, shopping or a boat ride on the Hudson River.

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

4.97 out of 5 average rating, 146 reviews

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!

The kitchen features modern appliances, including a black refrigerator and stainless-steel oven. A wooden dining table sits in the center, adorned with a bowl of fresh fruit. Shelves above display plants and kitchenware, while natural light filters through the windows, creating an inviting ambiance.

4.97 out of 5 average rating, 236 reviews

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.

A spacious bedroom features a queen bed adorned with simple linens. A large wooden barn door provides entry to the adjoining room. Two comfortable chairs sit beside a sleek television stand, with natural light filtering through large windows framed by greenery.

4.96 out of 5 average rating, 410 reviews

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!

A well-lit bedroom features a spacious bed covered with a soft white comforter. A large mirror leans against the wall, reflecting natural light. In the foreground, a vibrant green plant adds a touch of nature. The doorway leads to an inviting living area with warm lighting.

4.79 out of 5 average rating, 165 reviews

Comfy 2-BR Apt. Cozy & Convenient

Indulge in the charm of our delightful Kingston, NY apartment! Relax in two luxurious full beds amidst stunning trails, exquisite dining, and charming boutiques. Immerse yourself in vibrant Midtown, steps from the historic Stockade District. Rejuvenate, cook in our well-equipped kitchen, or dine on the private patio. Book now for an unforgettable stay! FUN FACT: Discover the fascinating historical gem of America's oldest corner, just a leisurely 10-15 minute stroll away.

A spacious kitchen features white cabinetry topped with a grey speckled countertop. Four black bar stools line the kitchen island. Modern appliances, including a stainless steel refrigerator and a gas stove, are visible, while ample natural light enters through the windows, brightening the room.

4.95 out of 5 average rating, 153 reviews

Majestic 3000 Sq ft Midtown Escape

Close to Polar Express & Frosty Fest! More room then you can ever imagine in our 3000 sq foot, 2 BR retreat In the heart of Kingston NY. 90 minutes from NYC. We offer modern amenities, cozy blankets, games and endless star gazing from our many windows at night. Just a 5 min walk to Ulster Performing Arts Center where you can catch a show, walking distance to local breweries, restaurants, bakery & coffee shop. Explore the boutiques in uptown Kingston and the waterfront!

The exterior of the Strand House is showcased, featuring a historic brick facade with large windows. A prominent sign reading 'STRAND HOUSE' is displayed above the entrance, which is accessed by a set of steps. Potted yellow flowers are placed near the entrance.

4.92 out of 5 average rating, 298 reviews

Historic Strand House - Unit 2 Woolsey Suite

Brand new luxury apartments in a restored historic building located in the heart of the historic Rondout District in downtown Kingston. A five minute walk from the waterfront, restaurants, bars, galleries, shops and marina. The Strand House consists of 4 units: (2) studios and (2) two-bedrooms all individually decorated and thoughtfully curated.

Popular amenities for Kingston family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 200 reviews

A waterfront home is shown from an elevated view, featuring an expansive deck with outdoor seating and a gazebo. Colorful kayaks are positioned along the water's edge, with lush trees showcasing autumn foliage in the background, contributing to the serene atmosphere.

Home in Saugerties

Waterfront Three bedroom in Saugerties w/ Hot Tub

4.96 out of 5 average rating, 372 reviews

A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

5 out of 5 average rating, 217 reviews

The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.

Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

4.92 out of 5 average rating, 340 reviews

A large, serene pool reflects the surrounding greenery and the stone facade of a historic guesthouse. Sun loungers are positioned beside the water, and well-maintained gardens and patios are visible in the backyard, inviting relaxation and outdoor enjoyment.

Guest house in Kingston

The Antique Stone House

4.98 out of 5 average rating, 139 reviews

The exterior of a modern cabin is showcased, featuring dark wood siding and large windows that invite natural light. A pair of black rocking chairs sits on the deck, complemented by a small metal table and logs stacked nearby. Lush green grass and scattered yellow wildflowers enhance the outdoor setting.

Cabin in Saugerties

Modern Cabin in the Woods with Hot Tub

4.99 out of 5 average rating, 200 reviews

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

4.98 out of 5 average rating, 105 reviews

A warm and inviting living space is seen, featuring a round wooden dining table surrounded by four rustic chairs. An adobe wood-burning fireplace is visible in the background, with seating arranged nearby for relaxation. Natural light flows in through a window, enhancing the cozy atmosphere.

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

4.99 out of 5 average rating, 139 reviews

Antique Uptown Charmer w/ Five-Star Modern Kitchen

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 1,029 reviews

An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.

Farm stay in High Falls

Dave's Milk Barn

A spacious living area features a futon decorated with patterned cushions and a striking red pool table. A light fixture with multiple bulbs hangs overhead, while a wall-mounted TV is visible in the background. Large pocket doors separate the living space from the bedroom.

4.98 out of 5 average rating, 201 reviews

Lovely 1 bedroom apt. with free parking in Rondout

4.93 out of 5 average rating, 180 reviews

A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

Home in Saugerties

Upstate Waterfront Saugerties Retreat-Near HITS

The exterior of the brick house is shown, featuring a green roof and a red door. A deck extends from the entrance, and a grassy lawn surrounds the property. Trees frame the background, indicating a tranquil, natural setting.

4.95 out of 5 average rating, 148 reviews

River Retreat, Walk to Hutton Bk Yds, Dog Friendly

Superhost

A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.

Apartment in Kingston

4.89 out of 5 average rating, 161 reviews

Offseason pricing Cozy & walking distance to town

A spacious living room features large windows allowing natural light to fill the area. A grand piano is positioned near a comfortable seating arrangement, which includes a sofa and chairs. A decorative area rug adds warmth, while framed artworks adorn the walls.

4.97 out of 5 average rating, 115 reviews

Large 2-BR apartment in historic waterfront home

5 out of 5 average rating, 432 reviews

A spacious master suite features a wooden accent wall and vaulted ceiling. A large bed with decorative pillows is positioned centrally, flanked by nightstands. In the background, a private bathroom is visible with modern fixtures and a wooden sink. Natural light filters through nearby windows.

Guest house in Woodstock

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

4.89 out of 5 average rating, 239 reviews

Flat in Newburgh

Special Nest w Private Entrance River View Porches

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 230 reviews

Apartment in Windham

Hideaway Windham/Hunter Fireplace, Snow & Skiing

4.95 out of 5 average rating, 104 reviews

Cabin in Lanesville

Only Ski In Out on Mtn | Hike, Golf, Fish, Unwind

4.82 out of 5 average rating, 198 reviews

Cottage in Kingston

Cottage with Private Deck on 8 acres of Woods

4.87 out of 5 average rating, 196 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

4.95 out of 5 average rating, 428 reviews

The living area features a comfortable couch and armchair, with large windows providing natural light and views of the outdoors. A wooden dining table with four chairs is positioned near the windows, while a coffee table sits in front of the couch. Shelves hold various books and decorative items.

Guest suite in New Paltz

Airy & Private Escape on Mountain Rest Road *Pool*

4.96 out of 5 average rating, 377 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

5 out of 5 average rating, 162 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills