Highland Falls Vacations from $760

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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.
Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,252, price is now $760 per person
$760
per person
Aug 5 - Aug 9
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,788 reviews)
Great location with short stroll to 5th Ave shops and directly opposite Central Park.

Reviewed on May 17, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Save 100% on your flight
Price was $2,732, price is now $1,505 per person
$1,505
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,903, price is now $1,664 per person
$1,664
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
Fabulous location right next to the ferry to Manhattan for a quick jump over to the Financial District. Nice area to wander around and grab a bite to eat. Views are insane. We went to the rooftop restaurant for the skyline views. Food was decent but atmosphere was the showstopper. Would stay again.

Reviewed on May 17, 2026

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Price was $3,710, price is now $2,161 per person
$2,161
per person
Jul 5 - Jul 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
5.6/10 (8 reviews)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar 17, 2024

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,711, price is now $1,010 per person
$1,010
per person
Jul 18 - Jul 24
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,511 reviews)
Chose the room because of the location but I was very happy. Its definitely for young people in the city for a good time. I came for a funeral. I really appreciated going back to positive energy and a building full of life and culture. Will stay again.

Reviewed on May 17, 2026

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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 refundable
$100 nightly
The price is $123 total per night from Jun 1 to Jun 2
$123 total
Jun 1 - Jun 2
Total with taxes and fees
8.6/10 Excellent! (695 reviews)
We stayed in Rm 123 and the room was extremely spacious. It was relatively clean. I would say it’s time for updates but it’s a solid motel and very close to West Point. The big negative is we could hear the walking around of the folks next door to us so if you are a light sleeper, that could wake ...

Reviewed on May 6, 2026

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
$154 nightly
The price is $188 total per night from May 25 to May 26
$188 total
May 25 - May 26
Total with taxes and fees
6.2/10 (818 reviews)
Plenty of parking. Great amenities.

Reviewed on May 5, 2026

FairBridge Inn & Suites at West Point
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
$125 nightly
The price is $143 total per night from May 26 to May 27
$143 total
May 26 - May 27
Total with taxes and fees
8.6/10 Excellent! (1,098 reviews)
Honestly, it was a great stay and I couldn't really complain about anything.

Reviewed on May 15, 2026

Hotel Nyack, a JdV by Hyatt Hotel
See all 846 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 $760 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.