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.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Sep 13 - Sep 17
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) 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

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (2,727 reviews)
Clean and close to attractions.

Reviewed on Aug. 7, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Sep 13 - Sep 17
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.4/10 Very Good! (544 reviews)
The location can’t be beat. You walk out your door and onto the beach. The staff is wonderful. All the kids working there are so attentive and sweet. We had a fantastic time. Cons: the room was so damp, everything we left with smelled. Windows didn’t open (they are all being replaced at some point but none in our building opened). The AC was old and I believe this is what caused the room to be damp. That plus no air circulation. The finishes are old. It feels tired. All of that said, I’d stay there again in a heartbeat but know what I’m signing up for. You’re not staying in a “luxury” room.

Reviewed on Aug. 6, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on Aug. 6, 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Oct 10 - Oct 14
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (621 reviews)
We loved our stay at the Lotte Towers! The rooms were very spacious for our family of 4. We were provided a fridge on request. The views were amazing. The lifts were quick to get us to the 58th floor! Our rooms were serviced twice daily. Cannot fault anything at Lotte would love to return one day!!

Reviewed on Apr. 15, 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
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 11 to Aug 12
CA $207
CA $234 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very Good! (609 reviews)
"Very friendly and helpful receptionist."

Reviewed on Aug. 4, 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 $143 per night from Aug 18 to Aug 19
CA $143
CA $168 total
Aug 18 - Aug 19
includes taxes & fees
6.2/10 (749 reviews)
"Quietness"

Reviewed on Aug. 3, 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 $128 per night from Aug 10 to Aug 11
CA $128
CA $149 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Excellent hotel with quality accommodations! The bed was super comfortable and the room beautifully decored. We enjoyed our 2night stay."

Reviewed on Aug. 5, 2025

Crowne Plaza Suffern - Mahwah by IHG
See all 755 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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highland Falls vacation package cost?
You can pick up a vacation package to this destination from CA $1,153 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.