New Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Wanderlustfemale

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best New Windsor Vacation Packages

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
The price is NT$3,241 per night from Dec 1 to Dec 2
NT$3,241
NT$3,666 total
Dec 1 - Dec 2
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Fast check in, great parking area.

Reviewed on 2025/11/16

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
The price is NT$3,969 per night from Dec 14 to Dec 15
NT$3,969
NT$4,490 total
Dec 14 - Dec 15
includes taxes & 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 2025/11/10

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
The price is NT$3,092 per night from Nov 29 to Nov 30
NT$3,092
NT$3,590 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Easy che kin nice, newly refurbished rooms.

Reviewed on 2025/11/13

Hampton Inn & Suites Poughkeepsie
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.

Discover the most popular places to visit in New Windsor

National Purple Heart Hall of Honor

5/5(1 review)

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

4/5(3 reviews)

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