
Pet-friendly vacation rentals in New Windsor
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in New Windsor
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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!

Foxglove Farm
Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

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!

Get Away to "Hygge" Tiny House on 75 Private Acres
Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Tranquil Tree-House on the beautiful Hudson River
Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

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.

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!

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!

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.

Hot Tub Bliss on 2 acres 16mi to West Point
Perfect Hudson Valley Getaway with king bed and 5 other beds, your own private hot tub, a spa like Master Bathroom with frameless shower, and heated tile floors make every step oh so cozy in both bathrooms! The house sits on a gorgeous two acres surrounded by trees and complete with a fire pit. Fast Wi-Fi , free off street parking just 16mi to West Point
Popular amenities for New Windsor pet-friendly home rentals
Pet-friendly house rentals

midcentury mod * POOL * walk out trail R2R /TOWN

Creekside cottage on 65 acres of land

Modern Upstate Gem Surrounded by Trees and Hot Tub

Balmville Mid-Century Gem & Work From Home Retreat

Modern 3BD West Point USMA House w/ HotTub!

Modern creekside cabin in the Catskills

ENTER HOME - Minimalistic style warm & inviting

The Waterfall House
Pet-friendly home rentals with a pool

E and T Getaway LLC

Entire Home (private pool), Event Friendly

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4Br Mountain Brook House on 130 acres w/ trails

Design Scandi Retreat, Heated Pool, Dogs Welcome

Airy & Private Escape on Mountain Rest Road *Pool*

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

Modern Upstate Cabin, near Rhinebeck NY
Private, pet-friendly home rentals

Dreamy Catskills mountain getaway w/ yoga studio

West Point/Bear Mountain/Hudson Valley Getaway

Tiny Cabin | Fire Pit | Screened Porch | Pets

Glenbrook Country Villa

Black A-Frame: Catskills Cabin

Beacon Modern victorian+garden—steps to mainstreet

Top Side

Bluebell - Kos Retreats @ Frogs Hollow Farm
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 $112 CAD per night before taxes and fees

Verified guest reviews
Over 470 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!
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- Times Square
- MetLife Stadium
- Central Park Zoo
- New York City Center
- Hunter Mountain
- Yankee Stadium
- Columbia University
- Mountain Creek Resort
- American Dream
- Bethel Woods Center for the Arts
- Rockefeller Center
- Radio City Music Hall
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Fairfield Beach
- Astoria Park
- The Metropolitan Museum of Art
- Bronx Zoo
- Resorts World Catskills
- Nickelodeon Universe
- Brotherhood, America's Oldest Winery
- Mohonk Preserve
- Mohawk Mountain Ski Area





