New Windsor Vacations from $327

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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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
Good pricing for the nice quality rooms

Reviewed on Jul 27, 2025

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
9.6/10 Exceptional! (51 reviews)
Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch

Reviewed on May 15, 2025

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
5.4/10 (1,006 reviews)
Nice reasonable place to stay

Reviewed on Jul 20, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
5.8/10 (1,008 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul 8, 2025

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
5.2/10 (1,001 reviews)
Toilet consistently running all night and TV remote not working

Reviewed on Jul 21, 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

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
$119 nightly
The price is $135 total per night from Aug 3 to Aug 4
$135 total
Aug 3 - Aug 4
Total includes taxes and fees
8.2/10 Very Good! (1,011 reviews)
Lovely 2 day stay
"The room was clean, the beds were super comfortable. Check in was easy."

Reviewed on Jul 27, 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
$178 nightly
The price is $201 total per night from Aug 10 to Aug 11
$201 total
Aug 10 - Aug 11
Total includes taxes and 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
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $154 total per night from Aug 25 to Aug 26
$154 total
Aug 25 - Aug 26
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Great price. Wonderful location. Will be back!"

Reviewed on Jul 31, 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.

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Frequently asked questions

How much does a New Windsor vacation package cost?
Offering great value package deals from $327 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.