New Windsor Holidays

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    Save up to S$134 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

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$172 per night from 27 Jul to 28 Jul
S$172
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Beautiful view and comfy bed and pillows"

Reviewed on 17 Jul, 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 S$257 per night from 3 Aug to 4 Aug
S$257
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"C"

Reviewed on 21 Jul, 2025

Homewood Suites Stewart Airport
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is S$167 per night from 3 Aug to 4 Aug
S$167
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (759 reviews)
"The property was awesome and the staff was excellent."

Reviewed on 21 Jul, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,003 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.

What to do in New Windsor

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

S$170
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

S$173
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

S$998
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in New Windsor

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.