Highland Falls Vacations from $1,152
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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.
1 Hotel Central Park
Manhattan
$2,181
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Excellent property in a perfect location- right across the street from Central Park and on the same block as a subway line which means super easy access to everywhere you’d want to go in the city.
The staff of the hotel are super friendly and helpful. The amenities are wonderful including a state-of-the-art fitness facility.
The on-site restaurant is also wonderful.
Reviewed on Oct 23, 2026
Ink 48 Hotel
Manhattan
$1,419
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,813 reviews)
Old and out of date. Drained carpet and stained furniture in the room. AC barely worked. Pictures online don’t match at all what the rooms look like.
Reviewed on Oct 24, 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
West Point Motel
156 Main Street Highland Falls NY
Fully refundable
$100 nightly
$123 total
Nov 9 - Nov 10
Total with taxes and fees
FairBridge Inn & Suites at West Point
17 Main St Highland Falls NY
$105 nightly
$128 total
Oct 26 - Oct 27
Total with taxes and fees
6.2/10 (861 reviews)
"I can't fully express my disappointment with this hotel. The website said newly remodeled rooms and the only thing that we saw newer than 1970 was the flooring. We booked this stay for a black tie event at the (unfortunately, sold out) Thayer Hotel, and were so uncomfortable with the condition of ..."
Reviewed on Oct 24, 2026
West Gate Inn Nyack
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
$97 nightly
$111 total
Nov 8 - Nov 9
Total with taxes and fees
7.4/10 Good! (1,494 reviews)
"I would not recommend this place to anyone. So unsanitary and unsafe. never again."
Reviewed on Oct 24, 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.
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 $1,152 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.
