New Windsor Vacations from $282

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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.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Save 100% on your flight
Price was $351, price is now $282 per person
$282
per person
Jan 22 - Jan 25
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9.2/10 Wonderful! (953 reviews)
Wasn’t the room i expected or was told I was going to get. Was checked in to a handicap accessible room

Reviewed on Nov 12, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
Price was $360, price is now $284 per person
$284
per person
Jan 8 - Jan 12
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.4/10 Very Good! (1,031 reviews)
Staff was extremely friendly and helpful, the room was clean and modern and the hot breakfast was delicious. I would definitely stay again.

Reviewed on Nov 10, 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Save 100% on your flight
Price was $354, price is now $283 per person
$283
per person
Jan 22 - Jan 25
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9.2/10 Wonderful! (1,004 reviews)
I was pleasantly surprised at how convenient the hotel was and would definitely stay here again. I really liked that there was a living room area as well as a bedroom area divided by a door and I was able to keep my cat in the living room area, which gave her space to move around. Honestly, the only cons where that the bed was a bit hard and the pillow was pretty flat other than that everything was pretty good including the water pressure.

Reviewed on Oct 24, 2025

Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was $654, price is now $524 per person
$524
per person
Feb 6 - Feb 9
found 8 hours ago
Roundtrip flight included
Dallas (DAL) to Newburgh (SWF)
8.6/10 Excellent! (1,088 reviews)
The room was extremely clean. The parking was good. Breakfast was not included for us.

Reviewed on Nov 10, 2025

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $359, price is now $297 per person
$297
per person
Feb 6 - Feb 9
found 8 hours ago
Roundtrip flight included
Dallas (DAL) to Newburgh (SWF)
8.6/10 Excellent! (1,000 reviews)
The hotel was very clean, enjoyed my stay would recommend

Reviewed on Nov 3, 2025

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Discover the most popular places to visit in New Windsor

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 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

Knox's Headquarters State Historic Site

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.

Knox's Headquarters State Historic Site

What to do in New Windsor

Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

Bear Mountain State Park+ BeaconTown 1-Day Tour From NY

$94
per adult
Bear Mountain State Park+ BeaconTown 1-Day Tour From NY
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
$104 nightly
The price is $118 total per night from Dec 1 to Dec 2
$118 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
Everything was good

Reviewed on Nov 10, 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
$127 nightly
The price is $144 total per night from Dec 7 to Dec 8
$144 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Front desk person at check in was amazing. She reminded me of my aunt. Bubbly personality. Breakfast staff was very accommodating. Very quiet hotel. I would definitely stay here again.

Reviewed on Nov 10, 2025

Homewood Suites Stewart Airport
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Nov 29 to Nov 30
$115 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
Clean room. Nice breakfast. Staff super friendly and helpful.

Reviewed on Nov 9, 2025

Hampton Inn & Suites Poughkeepsie
See all 996 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.

Find the Best New Windsor Vacation Packages

New Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
8,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brotherhood Winery, Palaia Vineyards Winery and Storm King State Park

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Frequently asked questions

How much does a New Windsor vacation package cost?
Offering great value package deals from $282 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.

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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.