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Pet-friendly vacation rentals in New Windsor

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in New Windsor

  • Total vacation rentals

    Explore 10 vacation rentals in New Windsor

  • Nightly prices starting at

    New Windsor vacation rentals start at $111 CAD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of New Windsor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across New Windsor rentals

  • 4.8 Average rating

    New Windsor stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in New Windsor

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews
Top guest favourite
A cozy living area is presented, featuring a soft beige sofa and a light armchair beside a wooden coffee table. A green plant adds a natural touch, and a light fixture hangs from the ceiling, while soft light filters in from a nearby window.
Home in Beacon

Beacon Creek House

Welcome to our serene oasis in Beacon, NY. If Gilmore Girls and Schitt’s Creek had a baby, it would be Beacon. Nestled beside a tranquil creek, our home features 2 cozy bedrooms, a stylish bathroom, and an open living space with a daybed. Designed with wabi-sabi aesthetics and eco-friendly materials. Just steps from Main Street and less than a 5 min drive from the train station, with scenic trails, shops and restaurants nearby. Book your stay and experience our artfully designed home and city!

4.99 out of 5 average rating, 164 reviews
Top guest favourite
Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

5.0 out of 5 average rating, 105 reviews
Superhost
A spacious living area features a comfortable gray sofa, accented by festive throw pillows. A light-colored coffee table sits in the center, surrounded by cozy armchairs. A large flat-screen TV is mounted on the wall, with natural light streaming through the nearby window.
Home in New Windsor

Farmhouse Getaway - 13mi to West Point

Gather with friends or family at our 1900s Hudson Valley farmhouse. This 3 bedroom unit offers one-level living with just one small step to the back deck—ideal for guests who prefer no interior stairs plus your own Hot Tub Bliss under the stars. Can accommodate large groups with 2 Kings, 1 Queen, plus 2 Queen sleeper sofas, twin daybed, twin trundle & floor mattress. Near Schunnemunk Mountain, Storm King, West Point and Newburgh waterfront. Fast Wi-fi, desks for remote work, free parking.

4.91 out of 5 average rating, 99 reviews
Guest favourite
The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.
Home in Cornwall-on-Hudson

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

4.93 out of 5 average rating, 191 reviews
Guest favourite
Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

4.89 out of 5 average rating, 274 reviews
Top guest favourite
A wooden porch leads to a vibrant purple door, framed by light-colored trim. Potted red flowers add color to the entrance, while natural light filters through the nearby trees, highlighting the rustic charm of the space.
Apartment in Cornwall-on-Hudson

Charming Efficiency

Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

4.98 out of 5 average rating, 247 reviews
Top guest favourite
A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.
Home in Newburgh

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

4.99 out of 5 average rating, 210 reviews
Top guest favourite
The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.
Home in Highland Falls

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

5.0 out of 5 average rating, 105 reviews
Top guest favourite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station.

4.95 out of 5 average rating, 368 reviews
Top guest favourite
Townhouse in Beacon

Pet-Friendly 3BR Retreat – Walk to Shops & Cafe

Welcome to your pet-friendly Beacon retreat! This spacious 3-bedroom, 1.5-bath townhouse is just one block from Main Street, placing you steps away from Beacon’s best coffee shops, restaurants, boutiques, and galleries. Enjoy a short walk to the Roundhouse, Hudson Valley Brewery, and other local favorites. The train station and Dia:Beacon museum are just a 6-minute drive, and the Loop Bus stop is only 2 blocks away for easy local transit.

4.96 out of 5 average rating, 389 reviews
Guest favourite
Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

4.92 out of 5 average rating, 180 reviews

Popular amenities for New Windsor pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley

Waterfront Lake House

4.94 out of 5 average rating, 138 reviews
Top guest favourite
A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.
Home in Cornwall-on-Hudson

Your West Point Academy Home Away from Home

4.99 out of 5 average rating, 126 reviews
Superhost
A fenced backyard features a stone patio equipped with two shaded loungers and a fire pit, complemented by vibrant umbrellas. An outdoor grill is positioned nearby, and a grassy area extends into the distance, bordered by lush greenery and a small shed.
Home in Beacon

Beacon Book-house off Main

4.78 out of 5 average rating, 111 reviews
Guest favourite
An open-concept living room features exposed brick walls and wooden beams. A sectional sofa and two modern chairs provide seating around a central coffee table. Bright light filters through sheer curtains on the windows, enhancing the cozy atmosphere.
Home in Beacon

Cozy chic Beacon retreat near Main St w hot tub

4.84 out of 5 average rating, 296 reviews
Top guest favourite
A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.
Home in Highland Falls

Modern 3BD West Point USMA House w/ HotTub!

4.99 out of 5 average rating, 114 reviews
Guest favourite
Home in Newburgh

Escape NYC! Spacious Withers Mansion Hudson Valley

4.84 out of 5 average rating, 264 reviews
Guest favourite
A functional kitchen features wooden cabinetry with a warm finish and a light-colored countertop. A stainless steel refrigerator is positioned alongside a compact microwave. The tile flooring adds practicality to the space, while a window with a lace curtain allows natural light to enter.
Home in Beacon

Mt hikes, city strolls river walks

4.96 out of 5 average rating, 284 reviews
Guest favourite
An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.
Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

4.82 out of 5 average rating, 107 reviews

Pet-friendly home rentals with a pool

Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.95 out of 5 average rating, 135 reviews
Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.88 out of 5 average rating, 220 reviews
Guest favourite
A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.
Guest suite in Holmes

Huge eclectic space w/ private pool. 1.5hr to city

4.97 out of 5 average rating, 224 reviews
Superhost
A spacious backyard features a heated pool surrounded by a stone patio, overlooking the scenic lake. Vibrant fall foliage adorns the landscape, and the serene water reflects the clear sky. A cozy home is visible, nestled against the lush greenery.
Home in Greenwood Lake

Luxury Villa w Lake View & Private Heated Pool

4.91 out of 5 average rating, 116 reviews
Guest favourite
A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.
Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

4.96 out of 5 average rating, 141 reviews
Guest favourite
An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.
Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

4.91 out of 5 average rating, 126 reviews
Top guest favourite
Cabin in Montgomery

Historic Cabin with Pool and Fire Pit

4.94 out of 5 average rating, 105 reviews
Top guest favourite
The exterior of a Mid Century Mod house is showcased at night, illuminated by soft outdoor lights. The building features large windows that reveal glimpses of the interior, while the surrounding lawn is landscaped with grass and scattered fallen leaves.
Home in New Paltz

midcentury mod hot tub*walk out trail R2R/Mohonk

4.98 out of 5 average rating, 548 reviews

Private, pet-friendly home rentals

Top guest favourite
A staircase is depicted, featuring dark wooden steps and a polished handrail. Natural light enters through a nearby window, illuminating the neutral-colored walls. The staircase leads upward, accentuating the vintage charm of the home.
Guest suite in Newburgh

Glenbrook Country Villa

4.93 out of 5 average rating, 682 reviews
Top guest favourite
A tiny house with large windows is nestled among the trees, offering a secluded retreat. A wooden deck with stairs leads to the entrance. An outdoor dining space with an umbrella and a propane grill is visible alongside a gravel area, complemented by a playful dog on the lawn.
Tiny homes in Wallkill

Get Away to "Hygge" Tiny House on 75 Private Acres

4.99 out of 5 average rating, 378 reviews
Top guest favourite
A navy blue sofa with bright yellow accent pillows is centered in the image. Behind the sofa, a well-organized shelving unit displays various books, decorative items, and plants. The light-colored walls and patterned rug contribute to a cozy living area.
Guesthouse in Beacon

Beacon Modern victorian+garden—steps to mainstreet

4.98 out of 5 average rating, 227 reviews
Top guest favourite
Apartment in Beacon

Family Friendly 3BR by Roundhouse

4.97 out of 5 average rating, 165 reviews
Guest favourite
An A-frame structure is positioned among trees, showcasing wooden siding and large windows. An outdoor deck features seating for relaxation, while warm light emanates from within. The surrounding landscape hints at a peaceful and wooded environment, enhancing the retreat's tranquil atmosphere.
Cabin in Carmel Hamlet

The Treehouse Lovenest

4.84 out of 5 average rating, 519 reviews
Guest favourite
The studio apartment is furnished with a Queen size bed dressed in neutral bedding, complemented by a cozy reclining chair. Brick walls and wooden accents create a warm environment. A small television is positioned for viewing, and a kitchenette area is visible in the corner.
Guest suite in Beacon

Cozy retreat, centrally located in Beacon NY

4.9 out of 5 average rating, 460 reviews
Guest favourite
A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.
Cottage in Philipstown

Modern Country Cottage by Bear Mountain

4.97 out of 5 average rating, 227 reviews
Guest favourite
The living room features a large blue sectional sofa that invites relaxation, positioned near oversized bay windows. A small dining table is visible, surrounded by chairs. Walls are adorned with decorative shelves, and a light fixture hangs from the ceiling, complementing the architectural details.
Apartment in Newburgh

Grant - A Tranquil One Bedroom Steps from River

4.92 out of 5 average rating, 270 reviews

Destinations to explore