Book Exclusive New Windsor Vacation Packages

Choose one or more items to build your trip:

New Windsor flight + hotel packages

Prices and availability subject to change. Additional terms may apply.
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
Jun. 7 - Jun. 9
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery are located nearby. Discover genuine guest reviews for Wildflower Farms, Auberge Resorts Collection along with the latest prices and availability – book now.
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Jun. 17 - Jun. 20
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
Stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Orange County Choppers are located nearby. Discover genuine guest reviews for Ramada by Wyndham Newburgh/West Point along with the latest prices and availability – book now.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2.5 out of 5
per person
May 30 - Jun. 1
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Stay at this business-friendly motel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Orange County Choppers are located nearby. Discover genuine guest reviews for Super 8 by Wyndham Newburgh/West Point Near Stewart Airport along with the latest prices and availability – book now.
Newburgh Inn

Newburgh Inn

2 out of 5
per person
Jul. 4 - Jul. 7
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a conference center. Popular attractions Orange County Choppers and Hamilton Fish Bridge are located nearby. Discover genuine guest reviews for Newburgh Inn along with the latest prices and availability – book now.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
May 30 - Jun. 1
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orange County Choppers and Hamilton Fish Bridge are located nearby. Discover genuine guest reviews for Howard Johnson by Wyndham Newburgh/West Point along with the latest prices and availability – book now.

Top New Windsor hotels deals

Red Roof Inn & Suites Newburgh – Stewart Airport

Red Roof Inn & Suites Newburgh – Stewart Airport

2 out of 5
915 Union Ave, New Windsor, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
per night
Apr. 28 - Apr. 29
Stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orange County Choppers and Hamilton Fish Bridge are located nearby. Discover genuine guest reviews for Red Roof Inn & Suites Newburgh – Stewart Airport along with the latest prices and availability – book now.
Pet-friendly
Pool
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $220 per night
CA $220
per night
May 6 - May 7
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orange County Choppers and Hamilton Fish Bridge are located nearby. Discover genuine guest reviews for Homewood Suites Stewart Airport along with the latest prices and availability – book now.
Hot tub
Pet-friendly
DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $173 per night
CA $173
per night
Apr. 28 - Apr. 29
Stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions McCann Ice Arena and Mid-Hudson Civic Center are located nearby. Discover genuine guest reviews for DoubleTree by Hilton Poughkeepsie along with the latest prices and availability – book now.
Breakfast available
Parking included
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $144 per night
CA $144
per night
Apr. 28 - Apr. 29
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby. Discover genuine guest reviews for La Quinta Inn & Suites by Wyndham Middletown along with the latest prices and availability – book now.
Pet-friendly
Pool
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free cancellation
The price is CA $163 per night
CA $163
per night
May 1 - May 2
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course are located nearby. Discover genuine guest reviews for HYATT house Fishkill/Poughkeepsie along with the latest prices and availability – book now.
Hot tub
Pet-friendly
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road, Poughkeepsie, NY
Free cancellation
The price is CA $144 per night
CA $144
per night
May 2 - May 3
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bananas Comedy Club and Casperkill Golf Club are located nearby. Discover genuine guest reviews for Hyatt Place Poughkeepsie / Hudson Valley along with the latest prices and availability – book now.
Pet-friendly
Pool
Don't see what you're looking for?
See all available properties in New Windsor
View all properties
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.

Popular places to visit

Image for Kristi Babcock Memorial Park

Kristi Babcock Memorial Park

Explore the great outdoors at Kristi Babcock Memorial Park, a lovely green space in New Windsor. You can attend a sporting event while in the area.

Kristi Babcock Memorial Park
Image for National Purple Heart Hall of Honor

National Purple Heart Hall of Honor

Rich with history, National Purple Heart Hall of Honor is a cultural attraction worth visiting in New Windsor. You can attend a sporting event while in the area.

National Purple Heart Hall of Honor
Image for New Windsor Cantonment State Historic Site

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

New Windsor Vacations

It's always a wise idea to learn a thing or two about your destination before you rush off on your travels. Circle New Windsor on your map now and start packing your bags for your next great adventure!

New Windsor is a neighborhood in Newburgh. You'll find it 4 miles (6 kilometers) southwest of the downtown area.

Ready to meet some of the locals? 29,000 people reside in Newburgh.

Places to visit in New Windsor

Be sure to get on your most avant-garde outfit before heading to Storm King Art Center. Putting on a variety of festivals, performances and exhibits throughout the year, it's a major part of the cultural landscape. Want some more nearby options? You don't have to be a prodigy to admire the vast lecture halls and intriguing stories of New York Military Academy. But that's not all. The world as we know it has been indelibly marked by war. Visit National Purple Heart Hall of Honor to learn more about the great battles of the past.

Where do you fly into for New Windsor?

Flying into LaGuardia Airport (LGA)? New Windsor is 50 miles (80 kilometers) from here. Grab a cup of coffee, wave down a cab and you'll be there in no time!

Frequently asked questions

How much are vacation packages to New Windsor?
CA $406 is all you’ll need for an amazing escape in New Windsor. Bundle your flights and hotel into a vacation package with Travelocity and watch all the savings pile up. With prices as good as these, you’ll want to start packing your bags now!
Where can I get the best vacation package deals for New Windsor?
It’s hard to top Travelocity when it comes to putting together your New Windsor package deal. There are at least 400 airlines and 665,000 worldwide properties to select from. Lock in your trip now and get ready to tick another amazing place off your must-visit list.
Why should I purchase my New Windsor vacation package via Travelocity?
Whether you’re on the hunt for the ultimate unplugged escape or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of different websites looking for the best deal — our Price Match Guarantee ensures you’ll always get the lowest possible price, and our team of customer service experts are available 24/7 should you need them.
Can I save on my New Windsor car rental if I book it with hotels and flights?
Most definitely — and booking one of our New Windsor vacation packages is the best way to go about this. Bundle any combination of a car, flight, hotel and experience and score great discounts. The more you book, the more you save. There are so many impressive sights in New Windsor to put on your bucket list, including Broadway (80 kilometersfrom New Windsor). Nothing beats exploring amazing places like this with the freedom of your own wheels.
What is the best time of year to go to New Windsor?
If budget is what’s driving your itinerary, you’ll score the best deals in . is typically the most expensive time of year. Most visitors head to this location during . If you want to avoid the hustle and bustle, visit during .
What is there to do in New Windsor?
Get out your travel itinerary and make a note of Storm King Art Center and New Windsor Cantonment State Historic Site. They are some of the top sights in New Windsor.
Where should I stay when visiting New Windsor?
A great night’s rest in New Windsor need not cost you a fortune, and the Red Roof Inn & Suites Newburgh – Stewart Airport (2.0 stars) and the Econo Lodge Near Stewart Inter (2.0 stars) are testament to that. Secure a room at one of these low-priced options and wake up feeling refreshed and ready to go.
Can I go on vacation to New Windsor at this time?
Learn all the info that’s important relating to quarantine policies and travel restrictions before you fly to New Windsor. Our Covid-19 Travel Advisor is full of useful advice to help make your vacation as smooth and carefree as possible.