New Windsor Vacations from $482

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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.

The Latest New Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
8.6/10 Excellent! (1,000 reviews)
Fast and easy check in

Reviewed on Aug 11, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 22 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8/10 Very Good! (463 reviews)
I liked that it was quiet I didn’t like that there was no guidance for the cycling trails o walking trails given

Reviewed on Aug 6, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 19
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.4/10 Very Good! (1,020 reviews)
The place was very clean and the staff was super friendly. Shout out to the guys working the break fast line .

Reviewed on Aug 12, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 19
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9.2/10 Wonderful! (775 reviews)
Place was great have stayed here many times.

Reviewed on Jul 30, 2025

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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

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

National Purple Heart Hall of Honor

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

What to do in New Windsor

Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

$159
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
See all activities in New Windsor

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
$115 nightly
The price is $130 total per night from Aug 13 to Aug 14
$130 total
Aug 13 - Aug 14
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"I stay at the Red roof Inn often and this is my favorite local hotel. I highly recommend anyone coming to the area to check the rates and come to the Red roof Inn because I promise you you will not be disappointed. 💙"

Reviewed on Aug 9, 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
$169 nightly
The price is $191 total per night from Sep 1 to Sep 2
$191 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Nice 2 bedroom suite easily accommodates family of 8 with 6 children( ages 2-13) 2 adults. The room was exceptionally clean.. i wiped down surfaces and floors before we settled in with lysol wipes and i was surprised there was no dirt. Food was decent, staff was very friendly and accommodating. I ..."

Reviewed on Aug 9, 2025

Homewood Suites Stewart Airport
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$94 nightly
The price is $112 total per night from Sep 11 to Sep 12
$112 total
Sep 11 - Sep 12
Total includes taxes and fees
7.2/10 Good! (509 reviews)
"Comfortable place to stay"

Reviewed on Aug 7, 2025

The Crossroads Hotel, Newburgh
See all 982 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.

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Frequently asked questions

How much does a New Windsor vacation package cost?
Offering great value package deals from $482 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?
You can generally find lower rates and greater availability in January, June and December. Explore our cheap New Windsor vacation packages and you could score some excellent off-season deals.
How many days is enough for New Windsor?
To get the most out of your New Windsor vacation, we recommend booking for 2 days. Divide your time between visiting Knox's Headquarters State Historic Site, New Windsor Cantonment State Historic Site and other top attractions, on top of exploring neighborhoods like Firthcliffe and Vails Gate. If you've got some spare time, add a day trip to your New Windsor vacation itinerary.
Is it worth booking a vacation package to New Windsor?
New Windsor offers everything you need for an amazing getaway. Begin your New Windsor vacation on a high note by exploring top attractions like National Purple Heart Hall of Honor.
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 your travel dates: The things you'd like to do in New Windsor and your favorite season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to experiences and flights. Your hotel will likely be the largest expense during your trip to New Windsor.
  3. Organize your New Windsor getaway with our trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to New Windsor together.
  4. Decide how many days away: Start by listing all the activities and sights you'd like to get to in New Windsor. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a New Windsor vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the highlights of New Windsor. Find all the exciting things to do in New Windsor with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later New Windsor vacation packages?
Your New Windsor trip is meant to be an escape from your daily routine, not a source of money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.