Highland Falls Vacations from $263

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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.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,051 reviews)
It was a good stay. I would recommend.

Reviewed on Jul 2, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
We love Loews Regency NYC. The staff is exceptional and the rooms are very comfortable.

Reviewed on Jun 29, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on Jun 25, 2025

Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
8.2/10 Very Good! (120 reviews)
Great reception! Raluca was so amazing and thoughtful!

Reviewed on Jun 20, 2025

Ruschmeyers Hotel

Ruschmeyers Hotel

3 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
7.8/10 Good! (44 reviews)
We had a great stay in Montauk. The property has been nicely updated and the staff go above and beyond! Kat and the staff were super friendly and helpful

Reviewed on Jun 18, 2025

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Discover the most popular places to visit in Highland Falls

West Point Museum

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.

West Point Museum

Highland Falls Hotel Deals

FairBridge Inn & Suites at West Point
FairBridge Inn & Suites at West Point
2 out of 5
17 Main St, Highland Falls, NY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Jul 6 to Jul 7
$129 total
Jul 6 - Jul 7
Total includes taxes and fees
6.2/10 (733 reviews)
"The location was not quite as close as the ad said. 2.5 miles from west point is not a 7 minute walk. For $500. they could have offered breakfast and upscale the unit."

Reviewed on May 30, 2025

FairBridge Inn & Suites at West Point
West Point Motel
West Point Motel
2.5 out of 5
156 Main Street, Highland Falls, NY
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $170 total per night from Jul 6 to Jul 7
$170 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (595 reviews)
"The comforter and duvet were silky material nd did not stay throughout the night. The AC in our room was loud and varied from too cold to humid warm. But very friendly staff, clean room, near to West Point for conviene."

Reviewed on Jun 27, 2025

West Point Motel
Hotel Nyack, a JdV by Hyatt Hotel
Hotel Nyack, a JdV by Hyatt Hotel
4 out of 5
400 High Avenue, Nyack, NY
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $163 total per night from Aug 3 to Aug 4
$163 total
Aug 3 - Aug 4
Total includes taxes and fees
8.4/10 Very Good! (1,018 reviews)
"Wonderful experience"

Reviewed on Jun 30, 2025

Hotel Nyack, a JdV by Hyatt Hotel
See all 762 properties in Highland Falls
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 $263 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.