Highland Falls Vacations from $382

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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.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $659, price is now $382 per person
$382
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Staff was amazing walls are super thin lmao rooms are smal but for the price your paying it’s worth it

Reviewed on Jan 14, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,156, price is now $571 per person
$571
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Cleanliness was excellent and the staff was very friendly

Reviewed on Jan 18, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $861, price is now $461 per person
$461
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The compressor from the heat pump in the room was so loud it would wake me up every time it kicked on all night long

Reviewed on Jan 17, 2026

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 $1,239, price is now $668 per person
$668
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
We had one of the best hotel experiences we’ve ever had. The atmosphere is young, welcoming, design-driven, and genuinely comfortable. Denise, Fior, and Angela truly embody what great hosts should be: warm, attentive, and effortless in their communication. Everything felt seamless from start to finish. We were pleasantly surprised with a room upgrade, and the facilities were modern, spotless, and extremely comfortable. It honestly felt unreal to have such a high-quality experience at a price we could afford in New York. The location couldn’t be bette, close to everything we needed and just steps from the subway. We even enjoyed a lovely complimentary wine tasting, which was a great touch. We’ll absolutely be back on our next trip to New York.

Reviewed on Jan 18, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,894, price is now $1,584 per person
$1,584
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
You need more dinner options in hotel

Reviewed on Jan 17, 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 Feb 2 to Feb 3
$113 total
Feb 2 - Feb 3
Total with taxes and fees
8.4/10 Very Good! (666 reviews)
Easy late checkin

Reviewed on Jan 14, 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
$99 nightly
The price is $111 total per night from Feb 1 to Feb 2
$111 total
Feb 1 - Feb 2
Total with taxes and fees
6.2/10 (800 reviews)
Well managed. Clean room.

Reviewed on Jan 10, 2026

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! (1,026 reviews)
The staff was friendly and helpful. It was a pleasant surprise to be offered a bottle of water and a warm cookie at check in. The room was clean and comfortable.

Reviewed on Jan 14, 2026

DoubleTree by Hilton Hotel Nanuet
See all 814 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 $382 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.