
Vacation rentals in New Windsor
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in New Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.

Quaint Apartment in Cornwall on Hudson
Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

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.

Hudson Valley Spacious Studio Private Secure
Spacious. Private entrance/ driveway. Park at door. Intimate for couples Roomy enough for 2 friends to share West Point parents/your cadet stays free Single traveler discount Welcome basket - Home-baked goodies 2 Super comfy queen beds Luxurious bathroom/heated Jacuzzi bath/seated walk in shower Desk/Wifi Private parking/entrance 42 inch tv Coffee/tea/morning muffins/ snacks Nearby- Stewart Airport Storm King Art Center USMA Woodbury Common DIA Beacon Hiking Wineries -No cooking allowed.

Cliff Top at Turtle Rock
Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

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.

Renovated Red 1890’s Hudson Valley Barn
Renovated barn in Mountainville, NY at the base of the Schunnemunk hiking trails. 1 mile from Storm King Art Center. 3 miles to Cornwall. 10 minutes from Woodbury Common Premium Outlet. 15 minutes to West Point. Private stairs & balcony leads to 500 square foot second-story space. You get the entire upstairs to yourself. The NYS Thruway does run between the house and the mountain. There is highway noise. TV has a ROKU. The WiFi signal is weak due to the metal siding on the barn.

Stylish Private Studio 1 block from Main St Beacon
Stylish, private bedroom & bath w/ self check-in private entrance. Garden/art/antiques/vintage bar-cart/mini-fridge/microwave/43in 4KTV/ black-out curtains/outdoor seating area. 1 block from Main St/3 min free shuttle/20 min walk from Metro-North station. Close to DIA&hiking trails. NOTE: -Ceilings are a bit low so if you are very tall, please contact before booking. -To ADD PET click "guests"scroll to bottom,select"pet"to pay fee for ONE pet $45 xtra for EACH additional pet

Riverview Rowhouse, a vintage modern home
Stylishly renovated 1890 Rowhouse in Newburgh's up-and-coming Washington Heights District. Enjoy your morning coffee with views of the Hudson River and Mountains. Just 75 minutes from NYC, this home is a short drive to the Newburgh Waterfront and Liberty Street's hip new shops and restaurants such as Ms. Fairfax, The Flour Shop, Liberty Street Bistro, Mama Roux, The Newburgh Brewery, and more. Close proximity to the Beacon Ferry and a short drive to the Beacon train station.

The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Historic 1 bedroom home in Cold Spring, NY
This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.
Popular amenities for New Windsor vacation rentals
Other great vacation rentals in New Windsor

Rustic Ranch w/ Fire Pit, Trails & Grazing Horses

2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area

Lander pied-à-terre with outdoor movie & dog park!

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

Arkadia House Mid-century retreat with pool & view

The Chrisearl

Home in Cold Spring- Farm Stay!

Expansive Views Whole Private House
Frequently Asked Questions
Are there family-friendly vacation rentals in New Windsor?
New Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in New Windsor?
Experience the best of New Windsor with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in New Windsor?
Four-legged friends are welcome in New Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in New Windsor?
Yes! Work meets play with ease at over 20 vacation rentals in New Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in New Windsor have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in New Windsor have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in New Windsor have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in New Windsor have free parking?
Absolutely! We offer over 10 house rentals with free parking in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in New Windsor

Total vacation rentals
Explore 40 vacation rentals in New Windsor

Nightly prices starting at
New Windsor vacation rentals start at € 52 per night before taxes and fees

Verified guest reviews
Over 2,840 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of New Windsor vacation rentals include wi-fi 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Times Square
- New York City Center
- Central Park Zoo
- Columbia University
- MetLife Stadium
- Hunter Mountain
- Mountain Creek Resort
- Yankee Stadium
- Rockefeller Center
- Bethel Woods Center for the Arts
- Radio City Music Hall
- Astoria Park
- Thunder Ridge Ski Area
- Fairfield Beach
- The Metropolitan Museum of Art
- American Dream
- Minnewaska State Park Preserve
- Resorts World Catskills
- Bronx Zoo
- Nickelodeon Universe
- Brotherhood, America's Oldest Winery
- Mount Peter Ski Area
- Kent Falls State Park
- Mohawk Mountain Ski Area





