Highland Falls Vacations from $395
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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
- Newark Hansbury Multi Level House
Jan 20 - Jan 24Newark Hansbury Multi Level House + Flight
Weequahic4 nights2.0 star property6.8/10 - (5 reviews)"nice"Reviewed September 10, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop LGA - ATL • Nonstop$665$395found 15 hours agoper traveler - JW Marriott Essex House New York
Jan 20 - Jan 24JW Marriott Essex House New York + Flight
Manhattan4 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop$1,724$991found 1 day agoper traveler - Parkway House Goshen Family-Friendly Bed & Breakfast
Jan 15 - Jan 18Parkway House Goshen Family-Friendly Bed & Breakfast + Flight
Goshen3 nights3.0 star property9.8/10 - Exceptional (46 reviews)"What a amazing property the stuff are amazin"Reviewed November 1, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop$738$456found 1 day agoper traveler - Night Hotel Broadway
Jan 7 - Jan 13Night Hotel Broadway + Flight
Manhattan6 nights3.0 star property7.4/10 - Good (78 reviews)"Place is not worth the money at all"Reviewed November 5, 2026Roundtrip • Dallas (DFW) - New York (JFK)DFW - LGA • Nonstop LGA - DFW • Nonstop - 1 Hotel Central Park
Dec 27 - Jan 21 Hotel Central Park + Flight
Manhattan6 nights5.0 star property9.0/10 - Wonderful (1,004 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop LGA - ATL • Nonstop$4,100$2,567found 1 day agoper traveler
Where to stay near Highland Falls
Newburgh
Discover Newburgh, a welcoming destination perfectly suited for family-oriented travelers and weekend getaway enthusiasts who will appreciate its vibrant city atmosphere and outdoor activities. With attractions like the contemporary art at Dia Beacon, the scenic beauty of Algonquin Park, and the educational environment of Mount Saint Mary's College, Newburgh offers diverse experiences for all ages. Located about 14 miles away from Highland Falls, it's an ideal base to explore the Hudson Valley. Choosing Newburgh for your stay ensures a blend of urban charm and natural beauty.
Fishkill
Plan your stay in Fishkill, a top-rated choice for family travelers and outdoor enthusiasts looking for a vibrant getaway. This charming city offers a variety of attractions, including the renowned Dia Beacon art museum, the historic Vassar College, and the scenic Fishkill Ridge, perfect for weekend adventures. With its appealing mix of education, shopping, and outdoor experiences, Fishkill serves as an excellent base, located about 23 miles by car from Highland Falls, making it a smart choice for your vacation.
West Point
If you are a history buff or an adventure seeker, look no further than West Point, known for its rich military heritage and outdoor experiences. Explore the fascinating West Point Museum and the beautiful landscapes of Bear Mountain State Park, perfect for families and those who appreciate culture. With its proximity to Highland Falls, just about 2 miles away by car, West Point makes for a smart choice for your stay, offering a blend of education, recreation, and local charm.
Beacon
Beacon stands out as a prime spot for weekend getaway travelers interested in nature and outdoor adventure. With attractions like Dia Beacon's contemporary art and the scenic vistas of Fishkill Ridge, visitors can immerse themselves in vibrant cultural and natural experiences. Located about 18 miles by car from Highland Falls, Beacon offers easy access to both relaxation and exploration. Choosing Beacon for your stay ensures a delightful blend of art, education, and the great outdoors.
Bear Mountain
Looking for the perfect spot? Bear Mountain is ideal for travelers seeking family-friendly adventures and nature experiences. With the stunning Bear Mountain State Park, the intriguing West Point Museum, and the beautiful Monteverde at Oldstone all nearby, you'll have plenty to explore. Located about 4 miles by car from Highland Falls, Bear Mountain offers easy access for your getaway. Choosing Bear Mountain for your stay ensures a memorable vacation filled with outdoor fun and captivating sights.
Discover the most popular places to visit in Highland Falls
Highland Falls Hotel Deals
FairBridge Inn & Suites at West Point
FairBridge Inn & Suites at West Point
Holiday Inn Express West Point by IHG
Holiday Inn Express West Point by IHG
The Thayer Hotel at West Point
The Thayer Hotel at West Point"Loved it!"
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain"The staff was very helpful when we had a dog barking at night. The room was very clean. We really enjoyed walking around the lake, When we complained about a cold shower it was fixed by the next day."
"We loved our stay! The staff was incredibly friendly and helpful. The amenities were wonderful, but mostly, this is a gorgeous property! For such an historic property, it is so comfortable and beautiful! We wish we could have stayed longer!"
"This property was beautiful!! Everything was clean and thoughtful, breakfast was homemade, with options from the staff. Staff were lovely, so friendly. Roy, the golden retriever was a cutie!! :)"
Hampton Inn Harriman Woodbury
Hampton Inn Harriman WoodburyFrequently Asked Questions
How much does a Highland Falls vacation package cost?
You can grab a vacation package to this destination from $395 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.