New Windsor Vacations from $250

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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
Price was $306, price is now $250 per person
$250
per person
Nov 6 - Nov 9
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.4/10 Good! (557 reviews)
A very clean room. Check in was quick. A friendly and professional staff member.

Reviewed on Sep 20, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Price was $1,211, price is now $984 per person
$984
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
8/10 Very Good! (479 reviews)
clean room, quiet, amazing shower

Reviewed on Sep 7, 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
Price was $515, price is now $418 per person
$418
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
5.4/10 (1,005 reviews)
Staff was nice, there was mold and a leak in the bathroom

Reviewed on Sep 12, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $626, price is now $519 per person
$519
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9.4/10 Exceptional! (831 reviews)
I really thanks Expedia helped to make this travel so smooth and get back of credits for the booking that is non refundable !!! I will for sure rememeber this trip and the great help of expedia !!!!

Reviewed on Sep 20, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $386, price is now $321 per person
$321
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
8.4/10 Very Good! (1,010 reviews)
Very nice and clean

Reviewed on Sep 20, 2025

Don't see what you're looking for?
See all available trips from Columbus to New Windsor
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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

Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

$135
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

$133
per adult
Beacon: Gourmet Beacon Food Tour
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
$109 nightly
The price is $123 total per night from Sep 28 to Sep 29
$123 total
Sep 28 - Sep 29
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Staff was nice, beds comfortable and rooms were clean! Great view of the Lake! Need some benches out there to sit and enjoy the view.No breakfast available Only coffee and juice was available."

Reviewed on Sep 15, 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
$172 nightly
The price is $194 total per night from Oct 19 to Oct 20
$194 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Everything was just fine no issues at all"

Reviewed on Aug 20, 2025

Homewood Suites Stewart Airport
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $117 total per night from Sep 28 to Sep 29
$117 total
Sep 28 - Sep 29
Total with taxes and fees
7.6/10 Good! (425 reviews)
"Clean, affordable and safe"

Reviewed on Sep 15, 2025

Quality Inn Poughkeepsie
See all 975 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 $250 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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