Highland Falls Vacations from $380

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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.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $761, price is now $380 per person
$380
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (9 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.

Reviewed on Aug 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,768, price is now $1,918 per person
$1,918
per person
Nov 17 - Nov 22
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug 21, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $753, price is now $404 per person
$404
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
The hotel itself was nice. There is truly nothing but senior citizens that stay here. We walked in and thought it was a nursing home. I’m not joking there must have been at least 60 70year olds when we walked in. They just take over the entire hotel. Again, the hotel itself is nice, but I think we would stay somewhere else knowing what we know now especially with two teenage boys with us.

Reviewed on Aug 28, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $3,486, price is now $1,889 per person
$1,889
per person
Oct 22 - Oct 27
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,001 reviews)
Exceedingly above my expectations

Reviewed on Jul 31, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,336, price is now $756 per person
$756
per person
Oct 17 - Oct 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (561 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound

Reviewed on Aug 18, 2025

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Discover the most popular places to visit in Highland Falls

West Point Museum

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 refundableReserve now, pay when you stay
$151 nightly
The price is $170 total per night from Sep 1 to Sep 2
$170 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (617 reviews)
"Perfect place to stay while visiting West Point. Room was super clean and staff were great. We will stay here anytime we are in town."

Reviewed on Aug 26, 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
$117 nightly
The price is $132 total per night from Sep 1 to Sep 2
$132 total
Sep 1 - Sep 2
Total with taxes and fees
FairBridge Inn & Suites at West Point
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59, Nyack, NY
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $98 total per night from Aug 31 to Sep 1
$98 total
Aug 31 - Sep 1
Total with taxes and fees
7.2/10 Good! (1,026 reviews)
"Steward was a great manager very helpful"

Reviewed on Aug 23, 2025

West Gate Inn Nyack
See all 759 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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Frequently asked questions

How much does a Highland Falls vacation package cost?
You can grab a vacation package to this destination from $380 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.