New Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 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 ₩138,663 per night from Feb 16 to Feb 17
₩138,663
₩156,862 total
Feb 16 - Feb 17
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
VERY CLEAN FRIENDLY STAFF!!!!

Reviewed on Jan 27, 2026

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 ₩189,323 per night from Feb 22 to Feb 23
₩189,323
₩214,172 total
Feb 22 - Feb 23
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
the room was clean and the hotel staff was nice.

Reviewed on Jan 29, 2026

Homewood Suites Stewart Airport
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is ₩128,927 per night from Feb 11 to Feb 12
₩128,927
₩145,848 total
Feb 11 - Feb 12
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Clean and good staff

Reviewed on Jan 27, 2026

Courtyard by Marriott Poughkeepsie
See all 1,031 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.

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.