Highland Falls Vacations from $543

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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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,010, price is now $543 per person
$543
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,026 reviews)
Location was great, staff was helpful and nice, I would recommend

Reviewed on Mar 25, 2026

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Queens
Price was $1,616, price is now $928 per person
$928
per person
May 29 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (201 reviews)
The Best location. Convenient. Subway just around the corner. Restaurants and groceries…. Can’t be better. Great apartment.

Reviewed on Mar 26, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $3,047, price is now $1,800 per person
$1,800
per person
Jun 7 - Jun 12
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (143 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.

Reviewed on Mar 24, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,757, price is now $1,056 per person
$1,056
per person
Jun 9 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,782 reviews)
The hotel was nice and the room was nice too especially for the price as compared to other hotels nearby and location was amazing!! Just steps away from Times Square. The area feels very safe even at night. The staff was helpful and friendly, they stored our luggage for free on day of checkout so we could walk around NYC a bit more. I'd definitely stay here again.

Reviewed on Mar 25, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,723, price is now $1,654 per person
$1,654
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,000 reviews)
Excellent staff, clean room, fantastic onsite restaurants.

Reviewed on Mar 10, 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 $113 total per night from Apr 9 to Apr 10
$113 total
Apr 9 - Apr 10
Total with taxes and fees
8.6/10 Excellent! (680 reviews)
Clean but dated

Reviewed on Mar 20, 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
$100 nightly
The price is $112 total per night from Apr 1 to Apr 2
$112 total
Apr 1 - Apr 2
Total with taxes and fees
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
$113 nightly
The price is $132 total per night from Apr 6 to Apr 7
$132 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (1,083 reviews)
Everything was great. Customer service was genuine and welcoming!!

Reviewed on Mar 23, 2026

DoubleTree by Hilton Hotel Nanuet
See all 817 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 $543 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.