Highland Falls Vacations from $347

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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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $627, price is now $347 per person
$347
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Very nice property. Clean. Friendly. Great rooms

Reviewed on Jan 4, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,133, price is now $522 per person
$522
per person
Feb 13 - Feb 15
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $929, price is now $482 per person
$482
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The hospitality and customer service is top tier. The ambiance is modern, clean, and the city view was incredible of the Empire State Building.Our family loves staying at the various Melia hotels.

Reviewed on Jan 8, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,294, price is now $1,246 per person
$1,246
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
This hotel was FABULOUS! The view you see if the view you get! STUNNING magazine worthy view of the Brooklyn bridge. Almost kid free. The rooftop bar and lounge had stunning views of the Brooklyn bridge and Hudson river. Just minutes away from Manhattan and close enough to walk to the Bridge. Room service was excellent. Very clean room.

Reviewed on Jan 3, 2026

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,465, price is now $799 per person
$799
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Traveled with family for the holidays . Felt safe , staff was friendly and helpful.

Reviewed on Jan 9, 2026

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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

West Point Motel

West Point Motel

2.5 out of 5
156 Main Street Highland Falls NY
Fully refundable
$100 nightly
The price is $113 total per night from Jan 25 to Jan 26
$113 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (663 reviews)
Yes

Reviewed on Dec 19, 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
$105 nightly
The price is $118 total per night from Jan 11 to Jan 12
$118 total
Jan 11 - Jan 12
Total with taxes and fees
6.2/10 (799 reviews)
Very good service

Reviewed on Dec 30, 2025

FairBridge Inn & Suites at West Point
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Feb 1 to Feb 2
$108 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,030 reviews)
Yes had a great stay . Will be back in the spring time .

Reviewed on Jan 4, 2026

DoubleTree by Hilton Hotel Nanuet
See all 811 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 $347 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.