Highland Falls Vacations from $1,129
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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 Riu Plaza Manhattan Times Square
Manhattan
$1,129
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.
Reviewed on Oct 25, 2026
JW Marriott Essex House New York
Manhattan
$1,143
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!
Reviewed on Oct 19, 2026
Hotel Riu Plaza New York Times Square
Manhattan
$1,561
per person
Dec 10 - Dec 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Location is superb. Gym is well equipped and in good repair. Breakfast was good - but ridiculously busy. Queues every day. We had two queen beds and a sofa bed which was fine for a family of four. The housekeeping was rubbish - they only cleaned the room one day in four nights, and no change of towels. When they did clean it they put the sofa bed away and removed the bedding. We got back late after a concert and waited an hour and a half for extra bedding to be brought up - despite multiple calls to the front desk-
Was really disappointing given it was late and the kids were tired. Put a
Dampener on what would have been a good hotel experience.
Reviewed on Oct 26, 2026
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See all available trips from Columbus to Highland Falls
View all tripsStay near popular Highland Falls attractions
West Point Museum
9.8/10 (25 reviews)
America's oldest federal museum showcases military artifacts from the Revolutionary War to modern times. Explore weapons, uniforms, and equipment while learning about the nation's military heritage at this free treasure.
Highland Falls Hotel Deals
West Point Motel
156 Main Street Highland Falls NY
Fully refundable
$100 nightly
$123 total
Nov 9 - Nov 10
Total with taxes and fees
FairBridge Inn & Suites at West Point
17 Main St Highland Falls NY
$105 nightly
$128 total
Oct 27 - Oct 28
Total with taxes and fees
6.2/10 (861 reviews)
"I can't fully express my disappointment with this hotel. The website said newly remodeled rooms and the only thing that we saw newer than 1970 was the flooring. We booked this stay for a black tie event at the (unfortunately, sold out) Thayer Hotel, and were so uncomfortable with the condition of ..."
Reviewed on Oct 24, 2026
West Gate Inn Nyack
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
$98 nightly
$112 total
Nov 8 - Nov 9
Total with taxes and fees
7.4/10 Good! (1,497 reviews)
"Nothing. The room was dirty & the bed had bed bugs. I checked out after being there just over two hours. Management couldn’t give me a different room ( not that I would taken it given the condition of the first room) They wanted to charge me for the full 3 days. I got them to bring it down to one ..."
Reviewed on Oct 25, 2026
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 $1,129 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.
