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.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Right across from the subway entrance, a Starbucks, and next to a Walgreens. Down the street, McD’s, Subway, Panda, CVS. Blocks away from Rockefeller Center. A block away from police and fire, felt safe the whole time. The property was modern and clean. We used the microwave in the lobby, our room had a fridge. Normal room size and not NY size, bed was comfortable and room was quiet! Definitely want to stay here again on the next trip.

Reviewed on Aug. 3, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Sep 3 - Sep 7
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
8.8/10 Excellent! (492 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul. 22, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (5,769 reviews)
Loved it all. Great experience!

Reviewed on Aug. 4, 2025

Ready to book your vacation to Highland Falls?

 

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Highland Falls Hotel Deals

West Point Motel

West Point Motel

2.5 out of 5
156 Main Street, Highland Falls, NY
The price is CA $207 per night from Aug 5 to Aug 6
CA $207
CA $235 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (607 reviews)
"Loved the area"

Reviewed on Aug. 2, 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
The price is CA $130 per night from Aug 5 to Aug 6
CA $130
CA $153 total
Aug 5 - Aug 6
includes taxes & fees
6.2/10 (747 reviews)
"Perfect for a solo female"

Reviewed on Jul. 12, 2025

FairBridge Inn & Suites at West Point
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
The price is CA $143 per night from Aug 10 to Aug 11
CA $143
CA $167 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Beautiful property."

Reviewed on Jul. 30, 2025

Crowne Plaza Suffern - Mahwah by IHG
See all 758 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Highland Falls vacation package cost?
You can pick up a vacation package to this destination from CA $860 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.