Pet-friendly holiday rentals in Kingston

4.99 out of 5 average rating, 158 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!

WalkabilityOutdoor spacesLaundry

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.

4.94 out of 5 average rating, 134 reviews

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.

Outdoor spacesWalkabilityNearby

The home's front facade is shown in evening light, with warm illumination emanating from the windows. The entrance features a traditional door framed by greenery, and side lights provide additional light. The pathway is lined with garden lighting, enhancing the welcoming appearance.

4.99 out of 5 average rating, 148 reviews

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.

WalkabilityOutdoor spacesValue

A spacious bedroom features a wrought iron bed dressed in neutral linens, accompanied by decorative pillows. Exposed brick and stone walls add character, while wooden beams and a warm area rug enhance the inviting atmosphere. Soft lighting from bedside lamps casts a gentle glow.

5.0 out of 5 average rating, 125 reviews

Garden apt with river views in downtown Kingston

Lovingly restored garden level apt in 1870's Victorian. Sweeping Hudson River views (with private patio) and just steps away from the entrance for the Kingston Point Rail Trail. Quick 1/2 mile walk to restaurants, shops and boats in Kingston's downtown historic West Strand. One mile walk to events at Hutton Brickyards. California king bed, Central A/C, washer-dryer. and full kitchen in unit! Designed by dog lovers (dogs 45 lbs and under are typically most comfortable due to size of space).

WalkabilityPetsBeach

4.97 out of 5 average rating, 104 reviews

An aerial view reveals a charming townhouse with a green metal roof and white exterior, surrounded by trees. Indoor spaces are characterized by natural light, showcasing a cozy seating area and dining table beneath exposed wooden beams, enhancing a sense of openness and warmth.

Townhouse in Kingston

Elegant Kingston Townhouse | Walk to Hot Spots!

Nestled in the esteemed Historic Stockade District or Uptown, this stunning townhouse offers the perfect blend of convenience and charm. Immerse yourself in the vibrant atmosphere of Kingston as you stroll to local favorites like Rough Draft Bar and Books, Kingston Bread, Stockade Tavern, Chleo, and so much more. Located just a short drive from hiking, swimming holes, skiing and more, the house is also the ideal jumping off point for discovering all that the Hudson Valley has to offer.

Outdoor spacesWalkabilityLayout

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, 185 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.

PetsWalkabilityHiking

4.99 out of 5 average rating, 150 reviews

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.

PetsWalkabilityCheckout

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.

4.81 out of 5 average rating, 186 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.

Outdoor spacesWalkabilitySleep quality

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

4.95 out of 5 average rating, 373 reviews

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!

WalkabilityOutdoor spacesLaundry

Serviced apartment in Kingston

A light-filled living area features a supple leather sectional sofa accompanied by a yellow armchair. A sleek side table rests in front of the fireplace, while a large flat-screen TV is mounted on the wall. Natural light filters through sheer curtains.

4.94 out of 5 average rating, 159 reviews

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.

WalkabilityPetsCheck-in

4.88 out of 5 average rating, 178 reviews

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

Historic Rondout Home | Walk to Waterfront

Welcome to our comfortable two-bedroom home in Kingston’s historic Rondout neighborhood. It’s an easy home base for couples, friends, families, and solo travelers—just a short walk from the waterfront and some of Kingston’s best restaurants and shops. *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston

Outdoor spacesWalkabilityBathroom

4.9 out of 5 average rating, 157 reviews

Tangerine Dream~king suite/ perfect for two

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.

PetsWalkabilityCheck-in

Popular amenities for Kingston pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A bright living area is showcased, featuring large windows that allow natural light to fill the space. A sectional sofa is paired with a red ottoman, and a decorative rug lies on the hardwood floor. A potted plant adds a touch of greenery to the room.

4.86 out of 5 average rating, 103 reviews

Historic Antique Uptown Farm House

Outdoor spacesPetsQuiet

4.9 out of 5 average rating, 195 reviews

The spacious great room features vaulted wooden ceilings and large windows allowing natural light to fill the space. Comfortable seating arrangements include a red chair and a variety of couches, while a stone fireplace stands as a central element. Warm wood finishes enhance the cozy environment.

Home in Hurley

Fox Lodge: Hudson Valley / Catskills Getaway

Outdoor spacesPetsAmenities

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

4.98 out of 5 average rating, 197 reviews

The Stone House

WalkabilityPetsCheck-in

The living room features a cozy arrangement with a large white sofa and striped chairs. A coffee table sits atop a textured rug. Natural light floods in through the windows, complementing the wooden beams and elegant chandelier. A piano and decorative elements add charm to the space.

4.97 out of 5 average rating, 177 reviews

The Stone Cottage: Close to HITS & Weekend Fun

PetsOutdoor spacesLong stay

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.

4.94 out of 5 average rating, 200 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

WalkabilityOutdoor spacesComfort

The bedroom features two twin beds with light bedding and decorative pillows. A wooden bedside table stands between the beds, alongside a vase of flowers. A round mirror and shelf adorn the wall, with natural light filtering through a nearby window.

4.9 out of 5 average rating, 156 reviews

Serene Kingston home on 1 acre! Kid & Pet Friendly

Outdoor spacesPetsCondition

4.98 out of 5 average rating, 131 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

WalkabilityPetsBathroom

4.95 out of 5 average rating, 167 reviews

River Retreat, Walk to Hutton Bk Yds, Dog Friendly

WalkabilityPetsParks

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 117 reviews

Cabin in Kingston

Modern Getaway in Kingston - 1.5hr from NYC

PetsOutdoor spacesNearby

4.9 out of 5 average rating, 142 reviews

An aerial view showcases the spacious home surrounded by trees and a manicured lawn. Outdoor seating is featured on the deck, illuminated by string lights. A fire pit area is visible, enhancing the outdoor gathering space for relaxation and socializing.

Chalet in Ruby

Enchanting Upstate Cabin w Pool, Firepit

WalkabilityOutdoor spacesCleanliness

The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.

4.79 out of 5 average rating, 133 reviews

Hudson River views with pool and hot tub

PetsOutdoor spacesValue

4.99 out of 5 average rating, 278 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

Outdoor spacesWalkabilityAccess

A spacious country house is showcased with a large wraparound deck featuring an umbrella and seating. The well-maintained grounds include greenery and a glimpse of an above-ground pool in the background, complemented by a clear blue sky.

4.93 out of 5 average rating, 127 reviews

Peaceful Hudson Valley Getaway

PetsOutdoor spacesRiver

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

4.98 out of 5 average rating, 128 reviews

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

WalkabilityOutdoor spacesIndoor spaces

A comfortable living room is highlighted by warm-toned walls and polished wood floors. A sectional sofa offers spacious seating, complemented by a rustic coffee table. A brick fireplace adds character, while natural light filters through white curtains on multiple windows.

4.94 out of 5 average rating, 140 reviews

Viewtop Farmhouse-Fall in the Hudson Valley

WalkabilityOutdoor spacesParking

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.

5.0 out of 5 average rating, 172 reviews

Upstate Modern Scandinavian Barn in the Catskills

Outdoor spacesPetsCondition

Private, pet-friendly home rentals

4.99 out of 5 average rating, 218 reviews

Cabin in Saugerties

Timberwall Ranger Station | Your Upstate Base Camp

WalkabilityOutdoor spacesCheckout

4.98 out of 5 average rating, 297 reviews

A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.

Cabin in Saugerties

Stunning 2-Bedroom A-Frame in the Woods with Sauna

Outdoor spacesWalkabilityLong stay

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, 438 reviews

Dog Friendly Uptown Apt Near Stockade + Backyard

WalkabilityPetsSolo travel

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, 236 reviews

Lovely 1 bedroom apt. with free parking in Rondout

Outdoor spacesPetsCheckout

4.99 out of 5 average rating, 126 reviews

Guest house in Hurley

Cozy Hillside Hideaway with Hot Tub

Outdoor spacesPetsHot tub

Religious building in Woodstock

4.99 out of 5 average rating, 235 reviews

1913 Church-History and Magic in the Forest

WalkabilityOutdoor spacesParking

A brick fireplace serves as a focal point, with several white candles arranged on the hearth. Natural light filters through a nearby window adorned with sheer curtains, illuminating the seating area with cozy cushions beside a built-in bookshelf.

4.8 out of 5 average rating, 264 reviews

In the Heart of Kingston

PetsOutdoor spacesSleep quality