New Windsor Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best New Windsor Vacation Packages

New Windsor Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is ₩148,316 per night from Aug 24 to Aug 25
₩148,316
₩167,775 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"no breakfast, but has pool"

Reviewed on Aug 2, 2025

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

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is ₩244,863 per night from Aug 17 to Aug 18
₩244,863
₩277,002 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Buen desayuno. Habitacion limpia y comoda."

Reviewed on Jul 25, 2025

Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is ₩193,896 per night from Aug 7 to Aug 8
₩193,896
₩219,352 total
Aug 7 - Aug 8
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"The hotel is unique and provides so many amenities! First we were greeted by very friendly and helpful staff at check in! Our room was clean and the lodge has a beautiful common area and view. The zoo, museums and park area is amazing! So many trails to take all within the park. Can’t wait to come ..."

Reviewed on Aug 2, 2025

Overlook Lodge at Bear Mountain
See all 992 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.

Frequently asked questions

How much does a New Windsor vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to New Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to New Windsor?
January, February and March are the best times to look for cheap New Windsor vacation packages. Opting to travel in quieter months means you can usually find reduced prices on accommodations and flights.
How many days is enough for New Windsor?
Allow at least 2 days for your New Windsor vacation if you're hoping to immerse yourself in everything that makes this destination special. Wander around popular areas, including Orange Lake and Vails Gate. Then tick off major sights such as National Purple Heart Hall of Honor and Knox's Headquarters State Historic Site. With a good itinerary, you can keep busy with room for some rest time too. Want to venture beyond New Windsor? Consider fitting in an excursion or two.
Is it worth booking a vacation package to New Windsor?
New Windsor is a good vacation destination with attractions like National Purple Heart Hall of Honor among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a New Windsor vacation promises a good time for everyone.
How to find the best New Windsor package deals?
Use Expedia's filters to find some fabulous New Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for New Windsor package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a New Windsor vacation as a package?
You can enjoy significant savings on your New Windsor getaway by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to New Windsor?
If you're considering a spontaneous New Windsor adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to New Windsor?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit New Windsor.
  2. Budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to New Windsor.
  3. Decide how long to go away for: Now that you're up to speed on New Windsor, you can work out the perfect length of your break. Create a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored New Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.