Highland Falls Vacations from $598
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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!
The Latest Highland Falls vacation packages
Price found within the past 48 hours. Click for updated prices.
42 Hotel
$598
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (994 reviews)
The room was real clean and comfortable. There was a light fixture not working in the bathroom but overall room was excellent.
Reviewed on Oct 4, 2026
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View all tripsStay near popular Highland Falls attractions
West Point Museum
9.8/10 (25 reviews)
America's oldest federal museum showcases military artifacts from the Revolutionary War to modern times. Explore weapons, uniforms, and equipment while learning about the nation's military heritage at this free treasure.
Highland Falls Hotel Deals
FairBridge Inn & Suites at West Point
17 Main St Highland Falls NY
$108 nightly
$132 total
Oct 6 - Oct 7
Total with taxes and fees
6.2/10 (854 reviews)
"The place was rundown, the parking lot was a disaster! The drive to the venue we were in town for was no “5 mile drive”…it was treacherous!!"
Reviewed on Oct 5, 2026
West Point Motel
156 Main Street Highland Falls NY
Fully refundable
$100 nightly
$123 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (745 reviews)
"Ample parking and safe. Staff are helpful. Air conditioning is good and room is clean."
Reviewed on Oct 4, 2026
West Gate Inn Nyack
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
$94 nightly
$108 total
Oct 28 - Oct 29
Total with taxes and 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.
Find the Best Highland Falls Vacation Packages
Highland Falls Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Westchester County Airport (HPN) |
Population | 3,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Brotherhood Winery, Palaia Vineyards Winery and Storm King State Park |
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Frequently asked questions
How much does a Highland Falls vacation package cost?
You can grab a vacation package to this destination from $598 on Expedia. However, how much your vacation to Highland Falls costs will depend on factors like the season, hotel choice 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 traveling in February, October and December. You'll typically find better prices on accommodations and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Highland Falls?
The ideal duration of your Highland Falls vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to tick off all the top attractions and explore some hidden spots along the way.
How to find the best Highland Falls package deals?
Use Expedia's filter tool to find some tempting Highland Falls package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Highland Falls package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Highland Falls vacation as a package?
You can enjoy significant savings on your Highland Falls break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Highland Falls?
If you're planning an impromptu Highland Falls adventure, browse 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 ahead.
Does Expedia offer Book Now, Pay Later Highland Falls vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Highland Falls trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
