New Windsor, NY

Travel Guide

A calm lake at sunset with trees and grass along the shore.
A large suspension bridge at night with illuminated cables and a central tower.
A calm lake with rocky shores and green hills in the background.
A rural landscape with autumn-colored trees, rolling hills, and a windmill in the foreground.
A pathway flanked by trees with autumn foliage, leading through a grassy field towards a hill.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
$99 nightly
The price is $117 total per night from Nov 8 to Nov 9
$117 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$104 nightly
The price is $122 total per night from Nov 9 to Nov 10
$122 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,008 reviews)
"Subject: Request for a Full Refund Due to Hotel Service Failures We were very excited about our stay at this hotel. Unfortunately, we had a very disappointing experience and were forced to cancel our stay because the hotel was not properly operating. Here is what happened: 1. Serious staff shortage ..."

Reviewed on Nov 3, 2026

Overlook Lodge at Bear Mountain
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
$94 nightly
The price is $109 total per night from Nov 29 to Nov 30
$109 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Poughkeepsie / Hudson Valley
See all 1,046 properties in New Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

New Windsor NY
Stay at this vacation home in New Windsor. Enjoy free WiFi, laundry facilities, and patios. Popular attractions New Windsor Little League and Motorcyclepedia ...
9.6/10 Exceptional! (9 reviews)
"Incredible and historic property, situated in a private enclosure of trees. Spacious for not only those staying overnight, but for our visiting guests who came over on a rainy day. The only recommendations would be to update the kitchen."

Reviewed on Oct 20, 2026

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres
1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
7.8/10 Good! (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."

Reviewed on Oct 12, 2026

1 Queen Bed | Non-Smoking, Kitchen
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush NY
Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Ellenville Fault Ice Caves and VerKeerderkill Falls are located nearby.
10/10 Exceptional! (26 reviews)
"The location was very impressive, the pictures don’t do it justice. Once you arrive, especially at night, the place looks majestic. It was the perfect calming and relaxing atmosphere it suggested. We took a beautiful walk along a peaceful trail surrounded by nature, and it was exactly what we needed. ..."

Reviewed on Nov 1, 2026

TRANQUIL MOUNTAIN SOLITUDE
See all properties in New Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular New Windsor attractions

National Purple Heart Hall of Honor

8.0/10 (11 reviews)
You can study the exhibits at National Purple Heart Hall of Honor, a museum with a storied past, during your trip to New Windsor. You can attend a sporting event while in the area.
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Frequently asked questions

Is New Windsor worth visiting?
New Windsor is worth visiting for its rich history and diverse dining. Travelers can explore significant sites like the National Purple Heart Hall of Honor and the New Windsor Cantonment State Historic Site. The area also offers a variety of culinary experiences, with options for Italian and Latin American cuisine.
When is the best time to visit New Windsor?
The best time to visit New Windsor is from May through September, when the climate is generally pleasant for exploring. For fewer crowds and better value, the quieter months of December through March are a good option. These months are cooler and may experience snow, offering a different kind of travel experience.
What is New Windsor known for?
New Windsor is known for the National Purple Heart Hall of Honor, which celebrates military service. Travelers can also explore the New Windsor Cantonment State Historic Site and enjoy outdoor activities at Kristi Babcock Memorial Park. The area also offers a strong Italian food culture.
What is a good itinerary length for New Windsor?
A good itinerary length for New Windsor is one to two days to visit key attractions like the National Purple Heart Hall of Honor and the New Windsor Cantonment State Historic Site. An extended stay of three to four days allows travelers to also enjoy Kristi Babcock Memorial Park and explore the local Italian, Latin American, and Asian dining options.
What are the top things to do in and around New Windsor?
New Windsor offers historical landmarks and natural spaces to explore, including:


How do I plan a trip to New Windsor?
To plan your trip to New Windsor, book flights and hotels on Expedia in advance. Explore landmarks like the National Purple Heart Hall of Honor and New Windsor Cantonment State Historic Site, along with Kristi Babcock Memorial Park. Consider a rental car for flexibility, and always have indoor backup plans for outdoor activities to account for weather.
What cuisines can you find in New Windsor?
In New Windsor, you can find Indian cuisine, with dishes like tandoori chicken, curries, naan bread, and samosas. Travelers can also enjoy Italian, Latin American (Mexican), and Asian (Chinese, Japanese) options, alongside various North American favorites.
Can I book a refundable hotel in New Windsor?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in New Windsor by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to New Windsor with Expedia?
Expedia makes it easier to plan your New Windsor trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in New Windsor?
The best choice depends on your travel style. Hotels in New Windsor can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my New Windsor trip on Expedia?
Once you've booked your New Windsor trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my New Windsor trip?
Expedia offers customer support before, during, and after your New Windsor trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to New Windsor?
If it's your first trip to New Windsor, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my New Windsor hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your New Windsor hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near New Windsor

A waterfront with a covered boat dock, a large red building, and a smaller building in the background.

Newburgh

A train crossing a steel bridge over a valley with autumn-colored trees.

Cornwall

A residential area surrounded by autumn-colored trees and rolling hills.

Cornwall-on-Hudson

A calm lake at sunset with trees and grass along the shore.

Highland Mills

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