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New Windsor vacation rentals

We found 276 vacation rentals — enter your dates for availability

Discover a selection of 10 homes and other vacation rentals in New Windsor that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, including WiFi and parking. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - New Windsor

Showing deals for:Jul 17 - Jul 24

Image gallery for West Point Family Retreat, 5 min walk to Thayer!

Exterior
9.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

9% off
Price is $566
$3,964 for 7 nights
All fees included
West Point Family Retreat, 5 min walk to Thayer!

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Find out more about New Windsor

Why visit New Windsor

  • Rich history: Discover historical sites and charming neighborhoods that showcase New Windsor's past.
  • Outdoor recreation: Enjoy a variety of parks and natural settings perfect for hiking, picnicking, and exploring.
  • Family-friendly activities: Find engaging attractions suitable for visitors of all ages, ensuring fun for the whole family.
  • Charming local atmosphere: Experience the warm hospitality and vibrant culture of nearby cities like New Paltz.
  • Diverse accommodations: Choose from a range of vacation rentals, including cozy homes and modern apartments.

Popular types of accommodation in New Windsor

Planning a getaway to New Windsor? Discover the perfect place to stay with a variety of vacation rental options including cozy houses, charming cottages, and modern apartments. Whether you're searching for townhouse rentals, single-family listings, or a spacious bedroom apartment, New Windsor has something to suit every traveler's needs. Explore your options and enjoy a comfortable stay in this beautiful area.

  • Houses: The top choice for travelers in New Windsor, offering spacious accommodations ideal for families and groups.
  • Cottages: A cozy and charming option, perfect for those seeking a quaint and intimate getaway.
  • Apartments: A convenient choice for visitors, providing home-like amenities in a central location.
  • Cabins: A rustic retreat for nature enthusiasts looking to immerse themselves in the great outdoors.
  • Villas: Luxurious properties that offer upscale living and stunning views for a lavish vacation experience.**

Top attractions near New Windsor

New Windsor, New York, is an ideal destination for families and outdoor enthusiasts alike. With a mix of national and urban parks, as well as historic houses, there's plenty to explore. Whether you're seeking cultural experiences or outdoor adventures, New Windsor offers a variety of attractions that cater to all travelers. Make the most of your vacation by discovering the rich history and natural beauty this charming area has to offer.

  • Dia Beacon: Situated 3 miles from New Windsor, Dia Beacon is a contemporary art museum known for its expansive galleries and stunning riverside views, offering a unique cultural experience.
  • United States Military Academy: Located 8 miles away, this prestigious academy provides a glimpse into American military history and offers guided tours of its historic campus.
  • Mount Saint Mary's College Newburgh: Just 2 miles from New Windsor, this modern university features vibrant city vibes and beautiful grounds, perfect for a leisurely stroll.

Things to do recommended for couples

For a romantic getaway in New Windsor, explore Brotherhood Winery and Benmarl Vineyards for delightful wine tastings amidst charming surroundings. Enjoy live music at The Falcon for an entertaining evening. These experiences promise to create memorable moments for you and your partner.

Things to do recommended for families

During your family vacation in New Windsor, enjoy a splashing good time at SplashDown Beach waterpark, explore sports at Kristi Babcock Memorial Park, and unwind at Bowdoin Park for some relaxation. These activities are perfect for creating lasting memories together.

Things to do recommended for groups

Experience shopping at Woodbury Common Premium Outlets for a variety of brands, enjoy a show at the nearby Ritz Theater for a dose of culture, or hit the greens at West Point Golf Course for a fun day outdoors with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in New Windsor

When you're planning a trip—be it with friends, family, or pets, or if you're considering an extended stay—it's important to prioritize your preferences effectively. Here are some helpful Vrbo booking tips for you.

  • Traveling to New Windsor with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to New Windsor with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to New Windsor: For many families, a vacation isn't truly fulfilling without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting New Windsor: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near New Windsor

New Windsor, New York, offers a delightful blend of family-friendly activities and scenic outdoor adventures. Explore the charming neighborhoods and nearby cities like New Paltz, where you can enjoy a vibrant atmosphere filled with friendly locals. Whether you're looking for luxury homes or budget-friendly rentals, New Windsor has something for everyone. With its picturesque surroundings, you'll create unforgettable memories during your vacation.

  • Newburgh: Situated just 2 miles from New Windsor, Newburgh is a vibrant city that offers a mix of family-friendly and outdoor experiences. Visitors can enjoy a variety of activities, including shopping at local centers and exploring educational venues. The city is home to picturesque landmarks such as the scenic lake and a well-equipped visitor center, which provide insights into the city’s rich history. Don't miss the historic sites that showcase Newburgh's past, making it a perfect spot for history enthusiasts and families alike.
  • Beacon: Located 3 miles from New Windsor, Beacon is a charming city known for its outdoor adventures and family-oriented activities. The city's artistic vibe is palpable, especially around local theaters and ski fields that attract both thrill-seekers and cultural aficionados. With stunning views of the nearby mountains and access to beautiful parks, Beacon is ideal for those looking to connect with nature while enjoying a vibrant community atmosphere. This city is perfect for a day trip full of exploration and excitement.
  • Fishkill: Just 8 miles from New Windsor, Fishkill is a welcoming city that combines family fun with urban conveniences. Visitors can indulge in shopping at its various centers and malls while also enjoying educational attractions suitable for all ages. Noteworthy landmarks include a symbolic landmark and a popular theme park, ensuring that there’s something for everyone in the family. The local visitor center provides helpful information, making Fishkill a great stop for tourists looking to explore the Hudson Valley region.

Best time to go to New Windsor

If you're planning a trip to New Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and November, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.3°F (-2.6°C)Light RainMostly SunnySlightly LowAverage
February29.1°F (-1.6°C)Light RainMostly CloudyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly CloudyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageSlightly Low
May59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
June67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
July73.2°F (22.9°C)Light RainMostly SunnySlightly HighSlightly High
August71.2°F (21.8°C)Light RainMostly SunnyAverageSlightly High
September64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
October53.2°F (11.8°C)Light RainMostly SunnySlightly LowAverage
November41.4°F (5.2°C)Light RainMostly SunnySlightly HighAverage
December33.4°F (0.8°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area to plan new adventures, resume your previous work, or manage your travel arrangements. You can easily find the properties you've saved or booked, organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lakeside setting of New Windsor is ready to explore

Enjoy the art galleries and other features of New Windsor. Travelers like the shopping, restaurants and lake in this welcoming and scenic city. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around New Windsor

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes New Windsor a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Ice Time Sports Complex (5.4 mi / 8.6 km)
  • Brotherhood Winery (7.8 mi / 12.6 km)
  • SplashDown Beach (7.8 mi / 12.6 km)
  • Benmarl Vineyards and Winery (8.3 mi / 13.4 km)
  • LEGOLAND® New York (16.5 mi / 26.6 km)
  • Robibero Winery (17.9 mi / 28.9 km)

Exploring the natural landscape of New Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, New Windsor is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Algonquin Park (3.6 mi / 5.8 km)
  • Storm King State Park (4 mi / 6.5 km)
  • Hudson Highlands State Park (4.3 mi / 7 km)
  • Fishkill Ridge (5.4 mi / 8.6 km)
  • Boscobel House and Gardens (6.2 mi / 10 km)
  • Oscawana Lake (10.7 mi / 17.3 km)

Traveling to and around New Windsor

The nearest airport is in Stewart Intl. Airport (SWF), located 3.6 mi (5.8 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Danbury, CT (DXR-Danbury Municipal), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the best area to stay in New Windsor, New York, United States of America when booking a vacation rental?
When considering a vacation rental in New Windsor, New York, the area around the Hudson River offers a wonderful experience. This picturesque neighborhood is known for its scenic views and proximity to outdoor activities. You can enjoy a leisurely stroll or a bike ride along the riverfront, which provides stunning vistas, especially at sunset.

In addition to its natural beauty, this area is conveniently located near attractions such as the historic Washington's Headquarters State Historic Site, where you can delve into American Revolutionary history. Another highlight is the New Windsor Cantonment State Historic Site, offering fascinating insights into the life of soldiers during that era.

The neighborhood features a variety of vacation rentals, from cozy cottages to larger homes, accommodating different group sizes and preferences.
How much does it cost to rent a vacation home in New Windsor?
Prices for vacation rentals in New Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in New Windsor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for New Windsor vacation house rentals?
You can find great discounts on house rentals in New Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best New Windsor ski resort rentals?
For the best ski resort rentals near New Windsor, travelers should consider areas like the nearby Hudson Valley and the Catskills region, which are within a reasonable driving distance. In the Hudson Valley, towns such as Beacon and Cold Spring offer a variety of rental options, including cozy cabins and modern homes that often feature amenities like wood-burning stoves, outdoor decks, and fully equipped kitchens. These properties provide a great base for exploring local attractions and enjoying winter sports.

Moving further into the Catskills, particularly in towns like Hunter and Windham, visitors can find vacation rentals that cater specifically to ski enthusiasts. These rentals typically include features such as ski-in/ski-out access, hot tubs, and spacious living areas ideal for relaxing after a day on the slopes. Many properties also provide convenient access to local ski shops and dining options, enhancing the overall experience for travelers.

The surrounding areas also offer opportunities for winter activities beyond skiing, such as snowshoeing and ice skating, with many rentals located near scenic trails and parks. See all ski-in-/ski-out rentals in New Windsor.
What is the most popular type of vacation rental accomodation in New Windsor?
In New Windsor, vacation houses are a popular choice, with several available throughout the area. These rentals typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor spaces, such as gardens or patios, superb for enjoying the scenic views of the Hudson Valley. Additionally, there are several apartments available, which provide a cozy alternative for travelers seeking a more compact living space. These apartments often come with essential amenities like kitchen facilities and comfortable living areas, allowing guests to feel at home during their stay.
Are there any family house rentals in New Windsor?
In New Windsor, there are several family-friendly house rentals available, making it a great choice for those traveling with kids. Properties in this area often feature spacious living rooms, fully equipped kitchens, and outdoor spaces where children can play safely. Many accommodations also include amenities like laundry facilities and Wi-Fi to ensure a comfortable stay.

Situated near attractions such as the historic town of Newburgh and the scenic Hudson River, families can enjoy local parks, playgrounds, and outdoor activities. Nearby, the Storm King Art Center offers vast grounds for exploration and art appreciation, while the area's proximity to hiking trails and nature preserves adds to the outdoor adventure options.
Can I rent a vacation home with a pool or hot tub in New Windsor?
In New Windsor, there are several vacation homes available for rent that come with pools and hot tubs, providing a great option for travelers looking to relax and unwind. This lovely area, located near the Hudson River, offers a mix of suburban tranquility and natural beauty. Many of the rental properties feature amenities such as private pools, hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens, making them ideal for family gatherings or small group retreats.

Additionally, the proximity to local attractions, including parks and scenic river views, enhances the overall experience, allowing guests to enjoy both relaxation and outdoor activities.
Can I find long-stay vacation rentals in New Windsor?
A long-stay vacation rental in New Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in New Windsor?
In New Windsor, travelers will find several pet-friendly house rentals that cater to those looking to enjoy a comfortable stay with their furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups.

The area offers a variety of rental options, from charming single-family homes to larger accommodations that can host more guests. Additionally, New Windsor is conveniently located near several parks and outdoor areas, providing ample opportunities for pet owners to take their dogs for walks or enjoy nature. Nearby attractions include the scenic Hudson River waterfront and various hiking trails that are pet-friendly, allowing for enjoyable outings with pets.
Are there any remote work vacation rentals in New Windsor?
In New Windsor, New York, there are several remote work vacation rentals available, with around 10 options to choose from. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi and comfortable workspaces. Guests can expect features such as cozy living areas, fully equipped kitchens for meal preparation, and sometimes dedicated office spaces to facilitate productivity during their stay.

The town is conveniently located near popular attractions like the Hudson River and the historic sites of West Point, providing a great blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any New Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in New Windsor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in New Windsor?
In New Windsor, vacation rentals often come equipped with a variety of popular amenities that enhance the guest experience. Most properties feature kitchens, allowing travelers to prepare their own meals, which is especially convenient for families or those planning longer stays. Onsite parking is generally available, providing ease of access for guests with vehicles. For those who may need to work during their stay, many rentals include desks and desk chairs, creating a comfortable workspace. Additionally, some properties may offer blenders, superb for making smoothies or preparing snacks.
When is the best time to visit New Windsor for a vacation rental?
The best time to visit New Windsor for a vacation rental is during the peak season from June to August. This vibrant period attracts many travelers eager to explore the region's outdoor activities, historical landmarks, and scenic beauty. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, summer offers an ideal climate for hiking, biking, and enjoying various events, including local festivals that showcase the area's rich culture.

July stands out as the most popular month, where you can immerse yourself in the lively option as families and friends gather to enjoy the summer sun. This is also a great time to take part in recreational activities along the Hudson River or visit nearby attractions such as the historic Washington's Headquarters State Historic Site.

For those looking for a more budget-friendly experience, consider planning your visit in December. In this season, this month brings its own charm with holiday festivities and a serene ambiance great for cozy getaways. You can enjoy the area's winter scenery while taking advantage of lower rental rates.

Ultimately, your ideal time to visit New Windsor will depend on whether you prefer the bustling summer atmosphere filled with activities or the peaceful charm of the winter season.
How early should I book a New Windsor vacation rental?
Book your New Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in New Windsor, New York, United States of America?
In New Windsor, visitors can explore several attractions that highlight the area's rich history and natural beauty. One of the main draws is the historic Washington's Headquarters State Historic Site, where George Washington commanded the Continental Army during the Revolutionary War. The site features a museum and beautiful grounds for leisurely walks.

Nature enthusiasts can enjoy the scenic views at the nearby Storm King Art Center, an expansive outdoor sculpture park that showcases large-scale works in a stunning landscape. The Hudson River offers opportunities for boating and fishing, with charming waterfront areas like the New Windsor Town Park providing picnic spots and walking trails.

For those interested in local history, the New Windsor Cantonment State Historic Site, which was a military encampment during the American Revolution, offers guided tours and reenactments.
Can I change or cancel my New Windsor home rental booking on Vrbo?
To find New Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the New Windsor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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