Highland Falls Vacation Packages
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Your Highland Falls Vacation
Organizing your next big getaway is a cinch with a Highland Falls vacation package. The neighborhood of Montrose, which is great for walking, makes a good starting point to discover the marvels of this unique city. Want to get out and explore? United States Military Academy, Bear Mountain State Park and Michie Stadium are some of the top places to visit during a trip to Highland Falls. Stop dreaming and start doing. Check out the many options on Expedia today and finally put your Highland Falls vacation plans into motion!
Top Highland Falls Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
CA $1,672
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
Facility can use more maintaining. Shower floor was cracked, door was leaking, no one came to clean the room in 4 days, staff did not try to accommodate our needs.
Reviewed on Aug 7, 2026
Ready to book your vacation to Highland Falls?
Highland Falls Hotel Deals
FairBridge Inn & Suites at West Point
17 Main St Highland Falls NY
Fully refundableReserve now, pay when you stay
CA $170
CA $216 total
Sep 1 - Sep 2
includes taxes & fees
6.2/10 (832 reviews)
"Security was very poor; no safety lock on door or window. We were on the ground floor and had to use a hanger to secure the window from opening. The parking lot was deteriorated and flooded. It had poor curb appeal. It didn't resemble was on the website."
Reviewed on Aug 5, 2026
West Point Motel
156 Main Street Highland Falls NY
Fully refundable
CA $140
CA $173 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (730 reviews)
"We have been trying out hotels/motels in the West Point vicinity for a couple years, so West Point Motel seemed an obvious choice for location. It was clean and had a reasonable rate for the location. There is a Mexican restaurant, drug store, and grocery store within walking distance. I was able ..."
Reviewed on Jul 23, 2026
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Fully refundable
CA $171
CA $199 total
Aug 30 - Aug 31
includes taxes & fees
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 Highland Falls attractions
West Point Museum
9.8/10 (25 reviews)
You can spend an afternoon exploring the galleries in West Point Museum in Highland Falls. Wander the riverfront or discover the area's mountain views.
Frequently asked questions
How much does a Highland Falls vacation package cost?
You can pick up a vacation package to this destination from CA $1,061 on Expedia. However, how much your vacation to Highland Falls costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Highland Falls?
If you're hoping to score a cheap Highland Falls vacation package, consider planning a trip in December, January and February. You'll usually find better prices on flights and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Highland Falls?
Generally, a handful of days is enough to tick off the main attractions during your Highland Falls vacation. But if you prefer to have more time to chill out or go on day tours, think about extending your trip.
How to find the best Highland Falls package deals?
Landing a cheap Highland Falls package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Highland Falls package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Highland Falls vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Highland Falls vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Highland Falls?
If you're planning a spontaneous Highland Falls vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Highland Falls?
- Choose when to get away: Check your diary and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Highland Falls.
- Budget wisely: As well as the cost of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Highland Falls.
- Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Highland Falls. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Highland Falls vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
