New Windsor Holidays

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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 3.014.118 ₫ per night from 10 Aug to 11 Aug
3.014.118 ₫
3.409.722 ₫ total
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Great.
"Exceeded expectations. Decent motel with large, clean rooms and social areas. Really friendly and helpful staff. Beautiful views over lake Washington."

Reviewed on 7 Aug 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 4.656.562 ₫ per night from 18 Aug to 19 Aug
4.656.562 ₫
5.267.736 ₫ total
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Clean updated room."

Reviewed on 3 Aug 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 State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is 3.748.316 ₫ per night from 25 Aug to 26 Aug
3.748.316 ₫
4.240.315 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The hotel is unique and provides so many amenities! First we were greeted by very friendly and helpful staff at check in! Our room was clean and the lodge has a beautiful common area and view. The zoo, museums and park area is amazing! So many trails to take all within the park. Can’t wait to come ..."

Reviewed on 2 Aug 2025

Overlook Lodge at Bear Mountain
See all 986 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.

Popular places to visit

Kristi Babcock Memorial Park

Kristi Babcock Memorial Park is just one of the places to see in New Windsor, so why not enjoy the other things to explore during your travels? You can attend a sporting event while in the area.

Kristi Babcock Memorial Park

New Windsor Cantonment State Historic Site

You can find out about the history of New Windsor when you stop by New Windsor Cantonment State Historic Site. You can attend a sporting event while in the area.

New Windsor Cantonment State Historic Site

Knox's Headquarters State Historic Site

You can spend an afternoon browsing the exhibits at Knox's Headquarters State Historic Site in New Windsor. Visit the shops and top-notch restaurants in this family-friendly area.

Knox's Headquarters State Historic Site

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.