New Windsor Vacation Packages

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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.

Top New Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Newburgh Inn

Newburgh Inn

2 out of 5
per person
Jul. 10 - Jul. 16
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
3.8/10 (32 reviews)
New owners bought it last year and are remodeling it. Doing a great job. New rooms are really nice.

Reviewed on May 21, 2024

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
Jul. 15 - Jul. 18
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.6/10 Exceptional! (18 reviews)
Good environment view, but the room is just okay in consideration of the price.

Reviewed on Feb. 25, 2024

Cottage Suites

Cottage Suites

3 out of 5
per person
Jul. 10 - Jul. 16
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
No reviews
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Jul. 10 - Jul. 16
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
6/10 (1,003 reviews)
I did have a patio but wasn’t able to go out there. The door wouldn’t open. Oops & I did have a microwave but it didn’t have the plate inside.

Reviewed on May 14, 2024

New Windsor Hotel 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
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 27 to May 28
CA $163
CA $184 total
includes taxes & fees
May 27 - May 28
8.2/10 Very Good! (1,000 reviews)
"It was clean and comfortable. Check inn was easy and the check-in person was very helpful in recommending places nearby to eat. It is also pet friendly with plenty of area to walk our dog."

Reviewed on May 16, 2024

Red Roof Inn & Suites Newburgh – Stewart Airport
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
The price is CA $243 per night from May 27 to May 28
CA $243
CA $275 total
includes taxes & fees
May 27 - May 28
9.2/10 Wonderful! (925 reviews)
"Beautiful hotel amazing outdoor space"

Reviewed on May 19, 2024

Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundable
The price is CA $194 per night from Jun. 5 to Jun. 6
CA $194
CA $217 total
includes taxes & fees
Jun 5 - Jun 6
8.6/10 Excellent! (1,001 reviews)
"Easy and safe area . Major highway nearby."

Reviewed on May 20, 2024

HYATT house Fishkill/Poughkeepsie
See all 970 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a New Windsor vacation package cost?
The most affordable New Windsor vacation package is CA $1,090, so your dream trip can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to build a package that suits your travel style.
How do I get a cheap travel package to New Windsor?
Bundle your bookings with Expedia to save big on your next getaway. With more than 550 airlines and 1,000,000 properties across the globe, your New Windsor vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not include one or more interesting experiences and tours? It’s an easy way to unlock even more savings. That vacation you’ve always dreamed of in New Windsor is much closer than you thought!
Where should I stay in New Windsor?
With so much to explore in New Windsor, it’d be handy for you to secure a room in a hotel near its attractions. Dia Beacon, Mount Saint Marys College Newburgh and Kristi Babcock Memorial Park are some fascinating ones to add to your itinerary.
What are the top hotels in New Windsor?
Many people like to stay at Red Roof Inn & Suites Newburgh – Stewart Airport in Vails Gate. If it’s your first time visiting New Windsor, you’ll get a warm welcome here.
How far in advance should I book my New Windsor vacation?
Savvy travelers always book early. Air carriers usually advertise flight tickets nearly 12 months in advance, and this is your chance to land some rock-bottom prices. Boss just told you to use up some vacation time next week? No problem! Expedia are never short of fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia New Windsor travel package include?
It comes down to what sort of getaway you’re contemplating. New Windsor travel deals can include flights, car rentals and hotels. You can mix and match to find the bundle that works for you! You can also add on activities and experiences after you’ve booked to pick up even bigger discounts.
What should I know before booking a New Windsor travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you’ve made your booking, add on fun stuff like activities or sightseeing tours. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a New Windsor Expedia vacation package?
The choice is all yours! Expedia has access to more than 550 airlines throughout the world, so you can design your New Windsor adventure according to your needs and budget.
If I'm not able to travel, can I cancel my New Windsor vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you’ve booked your New Windsor vacation package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in New Windsor

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 Knox's Headquarters 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

Image for Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

CA $1,056
Per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

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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.