Highland Falls Vacations from $440

Book a Hotel + Flight or Car together to unlock savings

Photo by 💋Priscilla 💋

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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $866, price is now $440 per person
$440
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,824, price is now $1,003 per person
$1,003
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
The staff go out of their way to make you feel at home

Reviewed on Oct 11, 2025

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,130, price is now $631 per person
$631
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (4,712 reviews)
Safe and walkable hotel near to restaurants

Reviewed on Oct 13, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,840, price is now $1,600 per person
$1,600
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,401, price is now $801 per person
$801
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
Great location - coffee and tea and little pastries in AM

Reviewed on Oct 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Highland Falls
View all trips

Discover the most popular places to visit in Highland Falls

West Point Museum

5/5(5 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.

West Point Museum

Highland Falls Hotel Deals

West Point Motel

West Point Motel

2.5 out of 5
156 Main Street, Highland Falls, NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $134 total per night from Nov 2 to Nov 3
$134 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (632 reviews)
"Convenient to West Point, which was the reason for our stay. Room was clean, but not really updated—which was fine."

Reviewed on Oct 3, 2025

West Point Motel
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
$122 nightly
The price is $138 total per night from Oct 14 to Oct 15
$138 total
Oct 14 - Oct 15
Total with taxes and fees
6.2/10 (763 reviews)
"The place was clean but very old. The pictures of the rooms on Expedia were not anything like the room we were given. It was very deceiving."

Reviewed on Oct 1, 2025

FairBridge Inn & Suites at West Point
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59, Nyack, NY
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Oct 14 to Oct 15
$100 total
Oct 14 - Oct 15
Total with taxes and fees
7.2/10 Good! (1,092 reviews)
"Staff was extreamly friendly. Great breakfast buffett."

Reviewed on Oct 9, 2025

West Gate Inn Nyack
See all 764 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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Highland Falls vacation package cost?
You can grab a vacation package to this destination from $440 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.