New Windsor Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

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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 ₩149,212 per night from Jan 1 to Jan 2
₩149,212
₩168,796 total
Jan 1 - Jan 2, 2026
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Great staff, comfy room

Reviewed on Dec 16, 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
The price is ₩205,793 per night from Dec 28 to Dec 29
₩205,793
₩232,802 total
Dec 28 - Dec 29
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Excellent room extremely clean and amazing and helpful staff

Reviewed on Dec 14, 2025

Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is ₩175,677 per night from Dec 21 to Dec 22
₩175,677
₩198,736 total
Dec 21 - Dec 22
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Parking was safe, secure, and easy.

Reviewed on Dec 7, 2025

Overlook Lodge at Bear Mountain
See all 1,010 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.

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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.