New Windsor Vacation Packages

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Your New Windsor Vacation

There's no better way to travel than with one of our vacation packages to New Windsor. The rich history and spectacular views are two of the convincing reasons to spend some time in this captivating city. Dia Beacon, Storm King Art Center and Ice Time Sports Complex are just some of the attractions you'll want to explore during your trip to New Windsor. A couple of quick clicks is all it takes to put together a tailored New Windsor vacation on Expedia.

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New Windsor Hotel Deals

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

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

915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
CA $123
CA $145 total
Aug 30 - Aug 31
includes taxes & fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

180 Breunig Rd New Windsor NY
CA $253
CA $299 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Great place to stay"

Reviewed on Aug 19, 2026

Homewood Suites Stewart Airport
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY
Fully refundable
CA $151
CA $178 total
Sep 13 - Sep 14
includes taxes & fees
Sleep Inn & Suites Middletown - Goshen
See all 1,013 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Stay near popular New Windsor attractions

Kristi Babcock Memorial Park

7.2/10 (9 reviews)
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.
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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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New Windsor Cantonment State Historic Site

8.2/10 (12 reviews)
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.
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New Windsor Little League

Catch an event at New Windsor Little League during your trip to New Windsor. While in this family-friendly area, you can savor the top-notch restaurants.
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Knox's Headquarters State Historic Site

8.4/10 (9 reviews)
You can spend an afternoon exploring the galleries in Knox's Headquarters State Historic Site during your travels in New Windsor. Check out the shops and top-notch restaurants in this family-friendly area.
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What to do in New Windsor

7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

CA $1,095
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

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 many days is enough for New Windsor?
To get the most out of your New Windsor vacation, we recommend staying for 2 days. Divide your time between discovering Algonquin Park, Orange County Choppers and other well-known attractions, on top of exploring neighbourhoods like Orange Lake and Vails Gate. If you've got some time to spare, add a day trip or tour to your New Windsor vacation itinerary.
Is it worth booking a vacation package to New Windsor?
New Windsor offers everything you need for an unforgettable escape. Begin your New Windsor vacation on a high note by checking out major attractions like National Purple Heart Hall of Honour.
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 travelling 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 favourite 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.

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