Highland Falls Vacations from $580

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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.
The Wayne Inn

The Wayne Inn

2 out of 5
Save 100% on your flight
Price was $1,126, price is now $580 per person
$580
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
6.8/10 (289 reviews)
Hair dryer was broken and no one came to repair it. There was a roach. The black out curtain was stuck so I couldn't adjust it. The gasket seal on the fridge door was faulty. The sink randomly leaked. The person who checked me in was oddly aggressive just because I didn't want to sign a blank receipt. Telling me I don't know how to check into hotels as if I'm not in my late 30s...

Reviewed on Feb 21, 2026

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Save 100% on your flight
Price was $7,952, price is now $4,489 per person
$4,489
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (3 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $3,769, price is now $2,175 per person
$2,175
per person
Jun 4 - Jun 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Just wonderful The staff at the hotel are magnificent Alway consistent always fantastic We will return time and time again! Concierge are the best in the city…

Reviewed on Apr 28, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,676, price is now $983 per person
$983
per person
Jul 1 - Jul 7
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,005 reviews)
We absolutely enjoyed our stay! The staff were excellent special shout out to Telik and Nick. Beautiful decor. I highly recommend it.

Reviewed on Apr 29, 2026

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,335, price is now $1,389 per person
$1,389
per person
Jul 18 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
2/10 (3 reviews)
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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! (689 reviews)
A nice quiet place to stay when visiting cadet son at West Point. An older motel that is well maintained and comfortable.

Reviewed on Apr 19, 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
$152 nightly
The price is $186 total per night from May 2 to May 3
$186 total
May 2 - May 3
Total with taxes and fees
6.2/10 (815 reviews)
4 hours before the power went off with no mention of when it would come back on. So my husband could no clean up before heading out for the day. So we had to check out 4 hours early.

Reviewed on Apr 27, 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
$124 nightly
The price is $142 total per night from May 11 to May 12
$142 total
May 11 - May 12
Total with taxes and fees
8.6/10 Excellent! (1,071 reviews)
Amazing industrial chic setting. Beautiful patio/ pool area. Food at conference was great. Only criticism: my room was concrete, walls, floors with high ceilings. The only rug on the room was under the bed and there was nothing soft in the room to absorb sound, even the chair was vinyl. It was relatively ...

Reviewed on Apr 30, 2026

Hotel Nyack, a JdV by Hyatt Hotel
See all 834 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 $580 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.