New Windsor Vacations

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    Save up to AEDĀ 5,000 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 ā€“ Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh ā€“ Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 327 per night from Nov 29 to Nov 30
AEDĀ 327
AEDĀ 387 total
29 Nov - 30 Nov
includes taxes & fees
8.4/10 Very Good! (1,016 reviews)
"It was really clean and staff were very friendly"

Reviewed on 11 November 2026

Red Roof Inn & Suites Newburgh ā€“ 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 AEDĀ 531 per night from Dec 11 to Dec 12
AEDĀ 531
AEDĀ 627 total
11 Dec - 12 Dec
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Great breakfast selection, very clean property overall"

Reviewed on 3 November 2026

Homewood Suites Stewart Airport
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 343 per night from Dec 13 to Dec 14
AEDĀ 343
AEDĀ 399 total
13 Dec - 14 Dec
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
See all 1,053 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)
This solemn museum honors Purple Heart recipients with interactive exhibits telling their stories of sacrifice. Explore the "Roll of Honor" database to discover personal narratives through artifacts.
See properties

Frequently asked questions

How much does a New Windsor vacation package cost?
You'll find cheap prices on Expedia for your New Windsor escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to New Windsor costs.
What are the cheapest months to go to New Windsor?
You can generally find lower rates and greater availability in January, February and March. Explore our cheap New Windsor vacation packages and you could get some great off-season deals.
How to find the best New Windsor package deals?
Finding a cheap New Windsor package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most pocket-friendly New Windsor package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a New Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights individually. Better still, you can personalize your New Windsor trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to New Windsor?
Secure incredible bargains by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu New Windsor escape.
How to plan a trip to New Windsor?

  1. Choose when to travel: Check your schedule and get packing. Your favorite season and the available activities will also help you decide when to escape to New Windsor.
  2. Set a budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to New Windsor. Then, choose a hotel that fits your budget, whether that's an affordable option or a more upscale getaway.
  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 vacation. Pull together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored New Windsor vacation package.