Highland Falls Vacation Packages

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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!

Top Highland Falls Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,314, price is now CA $1,306 per person
CA $1,306
per person
Sep 17 - Sep 20
found 8 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,213 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $3,818, price is now CA $2,098 per person
CA $2,098
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,623 reviews)
Great check in, nice staff. Very small but well laid out room that was clean and confortable. Very quiet and great location. Will stay here again-

Reviewed on Jul 28, 2026

Residence Inn Marriott New York Downtown Manhattan/WTC Area

Residence Inn Marriott New York Downtown Manhattan/WTC Area

3.5 out of 5
Manhattan
Price was CA $2,328, price is now CA $1,311 per person
CA $1,311
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,007 reviews)
Staff were great. The room was ok for the price.

Reviewed on Jul 28, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $8,719, price is now CA $4,982 per person
CA $4,982
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (689 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,911, price is now CA $1,721 per person
CA $1,721
per person
Oct 14 - Oct 18
found 7 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
Perfect location, very attentive staff, beautiful room.

Reviewed on Jul 29, 2026

Ready to book your vacation to Highland Falls?

 

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Highland Falls Hotel Deals

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
The price is CA $146 per night from Aug 2 to Aug 3
CA $146
CA $187 total
Aug 2 - Aug 3
includes taxes & fees
6.2/10 (830 reviews)
"It was clean and staff waited for us to check in late. Left key on desk to check out. Furniture was old and mismatched but the bed was comfortable"

Reviewed on Jul 15, 2026

FairBridge Inn & Suites at West Point
West Point Motel

West Point Motel

2.5 out of 5
156 Main Street Highland Falls NY
Fully refundable
The price is CA $169 per night from Aug 11 to Aug 12
CA $169
CA $208 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (730 reviews)
"We have been trying out hotels/motels in the West Point vicinity for a couple years, so West Point Motel seemed an obvious choice for location. It was clean and had a reasonable rate for the location. There is a Mexican restaurant, drug store, and grocery store within walking distance. I was able ..."

Reviewed on Jul 23, 2026

West Point Motel
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
The price is CA $179 per night from Aug 26 to Aug 27
CA $179
CA $243 total
Aug 26 - Aug 27
includes taxes & fees
Hotel Nyack, a JdV by Hyatt Hotel
See all 823 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.
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Stay near popular Highland Falls attractions

West Point Museum

9.8/10 (25 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.
See properties

Frequently asked questions

How much does a Highland Falls vacation package cost?
You can pick up a vacation package to this destination from CA $1,306 on Expedia. However, how much your vacation to Highland Falls costs will depend on your hotel choice, season 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 planning a trip in December, January and February. You'll usually find better prices on flights and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Highland Falls?
Generally, a handful of days is enough to tick off the main attractions during your Highland Falls vacation. But if you prefer to have more time to chill out or go on day tours, think about extending your trip.
How to find the best Highland Falls package deals?
Landing a cheap Highland Falls package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Highland Falls package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Highland Falls vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Highland Falls vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Highland Falls?
If you're planning a spontaneous Highland Falls vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Highland Falls?

  1. Choose when to get away: Check your diary and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Highland Falls.
  2. Budget wisely: As well as the cost of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Highland Falls.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Highland Falls. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Highland Falls vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.