New Windsor Vacations

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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 AED 364 per night from Mar 23 to Mar 24
AED 364
AED 411 total
includes taxes & fees
23 Mar - 24 Mar
8.2/10 Very Good! (1,000 reviews)
one night stay - everything was great
"a great stay overall, things were clean, it was very quiet, wonderfully comfortable mattress, friendly staff, very convenient ... it would have been very nice if there was coffee available in the lobby (24×7) or to have a personal coffee maker in the room"

Reviewed on 16 March 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 AED 434 per night from Mar 27 to Mar 28
AED 434
AED 491 total
includes taxes & fees
27 Mar - 28 Mar
9.2/10 Wonderful! (980 reviews)
"The complimentary breakfast was A1!"

Reviewed on 17 March 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
Fully refundableReserve now, pay when you stay
The price is AED 372 per night from Mar 23 to Mar 24
AED 372
AED 420 total
includes taxes & fees
23 Mar - 24 Mar
8/10 Very Good! (1,001 reviews)
Love staying here
"It was great thank you"

Reviewed on 18 March 2025

Overlook Lodge at Bear Mountain
See all 977 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 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.

Discover the most popular places to visit in New Windsor

Kristi Babcock Memorial Park

Kristi Babcock Memorial Park is just one of the places to see in New Windsor, so why not enjoy the other things to explore during your travels? You can attend a sporting event while in the area.

Kristi Babcock Memorial Park

National Purple Heart Hall of Honor

5/5(1 review)

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.

National Purple Heart Hall of Honor

New Windsor Cantonment State Historic Site

You can find out about the history of New Windsor with a stop at New Windsor Cantonment State Historic Site. You can attend a sporting event while in the area.

New Windsor Cantonment State Historic Site