New Windsor Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in New Windsor
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
S$135
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Very nice staff and clean room."
Reviewed on 9 Aug, 2026
Homewood Suites Stewart Airport
180 Breunig Rd New Windsor NY
S$260
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Very clean hotel and rooms. Friendly and helpful staff. The pool are was also nice and clean and the hotel was nice and quiet. The breakfast was good and gave lots of options to choose from."
Reviewed on 9 Aug, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
S$163
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,035 reviews)
"Great stay"
Reviewed on 10 Aug, 2026
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.
Stay near popular New Windsor attractions
Kristi Babcock Memorial Park
7.2/10 (9 reviews)
This community park honours local resident Kristi Babcock with modern sports facilities and a rubberized playground. Families can enjoy the walking path, pavilion areas, and seasonal town events like annual Community Day.
National Purple Heart Hall of Honor
8.0/10 (11 reviews)
This solemn museum honours Purple Heart recipients with interactive exhibits telling their stories of sacrifice. Explore the "Roll of Honour" database to discover personal narratives through artefacts.
New Windsor Cantonment State Historic Site
8.2/10 (12 reviews)
Step back in time at the Continental Army's final Revolutionary War encampment. Costumed interpreters bring history to life through military drills and craftsmanship demonstrations in reconstructed log huts.
Knox's Headquarters State Historic Site
8.4/10 (9 reviews)
Step back in time at this Revolutionary War command centre where General Henry Knox once strategized. The guided tour through the 18th-century stone house reveals authentic period furnishings and military artefacts.
New Windsor Little League
Catch an event at New Windsor Little League during your trip to New Windsor. While in this family-friendly area, you can savour the top-notch restaurants.
What to do in New Windsor
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
S$1,005
per traveller
Frequently asked questions
How much does a New Windsor holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to New Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to New Windsor?
January, February and March are the best times to look for cheap New Windsor holiday packages. Opting to travel in quieter months means you can usually find reduced prices on accommodation and flights.
How many days is enough for New Windsor?
Allow at least 2 days for your New Windsor holiday if you're hoping to immerse yourself in everything that makes this destination special. Wander around popular areas, including Orange Lake and Vails Gate. Then tick off major sights such as National Purple Heart Hall of Honour and Knox's Headquarters State Historic Site. With a good itinerary, you can keep busy with room for some rest time too. Want to venture beyond New Windsor? Consider fitting in an excursion or two.
Is it worth booking a holiday package to New Windsor?
New Windsor is a good holiday destination with attractions like National Purple Heart Hall of Honour among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a New Windsor holiday promises a good time for everyone.
How to find the best New Windsor package deals?
Use Expedia's filters to find some fabulous New Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for New Windsor package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a New Windsor holiday as a package?
You can enjoy significant savings on your New Windsor getaway by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to New Windsor?
If you're considering a spontaneous New Windsor adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to New Windsor?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit New Windsor.
- Budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to New Windsor.
- Decide how long to go away for: Now that you're up to speed on New Windsor, you can work out the perfect length of your break. Create a rough plan and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored New Windsor holiday package.
* 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.
