New Windsor Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in New Windsor

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 S$161 per night from 3 Dec to 4 Dec
S$161
includes taxes & fees
3 Dec - 4 Dec
8.2/10 Very Good! (1,000 reviews)
"My stay was nice and convenient"

Reviewed on 24 Nov,2024

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 S$206 per night from 4 Dec to 5 Dec
S$206
includes taxes & fees
4 Dec - 5 Dec
9.2/10 Wonderful! (952 reviews)
"Such a nice experience! easy and very cordial check-in! easy check out! clean rooms! great breakfast buffet!"

Reviewed on 10 Nov,2024

Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is S$181 per night from 1 Dec to 2 Dec
S$181
includes taxes & fees
1 Dec - 2 Dec
7.8/10 Good! (1,005 reviews)
"A beautiful property, wonderful staff, and very well-kept clean rooms."

Reviewed on 22 Nov,2024

Overlook Lodge at Bear Mountain
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.

Frequently asked questions

How much does a New Windsor holiday package cost?
The most affordable New Windsor holiday package is , 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 holiday 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 holiday 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 holiday?
Savvy travellers 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 holiday 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 holiday 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 holiday 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 holiday 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.

What to do in New Windsor

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.