Plan your trip

A suspension bridge over a river, surrounded by dense forest and hills.

Highland Falls Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Check prices for these dates

    Check prices for these dates, December 13 – 14, 2026

    View in a map

    Our top choices for Highland Falls vacation rentals

    1. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

    A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

    2. Cozy 1-bedroom retreat minutes from West Point!

    Living area

    3. Local Artist Inspired | Walk to WestPoint + King Bed

    A living room with a sectional sofa, a coffee table, and a ceiling fan.

    4. 3BR Near West Point | Coffee Bar | Sleeps 6

    A hallway with a wooden door, a black table with a sign, and large green plants.

    5. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

    A bathroom with a black vanity, a glass bowl sink, and a mirror above it.

    6. Lovely 3BR Home with parking-Walk to WP Gate!

    A room with hardwood flooring, a flat-screen TV on a stand, a white door, and a staircase leading to another level.

    7. Fabulous 3bdrm Home w/parking!

    A house with a white front door, a small porch with a white railing, and a window with a green curtain.

    8. Mountain-View 2BR Steps from Thayer Gate

    A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

    9. Walk to WP Gate + Free Parking!

    A two-story house with a porch and a gated driveway.

    10. Perfect 2BR with Free Parking! Walk to West Point!

    A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

    11. Hudson Valley/West Point Retreat w/ parking!

    A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

    12. 3BR West Point Retreat-3min to Back Gate+ King Bed

    A blue house with a white porch, a welcome sign, and a mailbox.

    13. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

    A house with a view of a bridge and mountains.

    14. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

    A wooden shed with two kayaks mounted on its side.

    15. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

    A room with a glass table and chairs, a flat-screen TV on the wall, and a view of a beach and buildings.

    16. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

    A brick building with a sign reading 'Lobby' in front.

    17. 1 King Bed | Non-Smoking, Kitchen, Shower

    A compact kitchenette with a microwave, stove, sink, and a small dining area.

    18. Contemporary Cozy Cottage

    A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

    19. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

    A brick building with a storefront featuring a sign for 'LUXE Optique'.

    20. Private River View Deck · Walk Downtown

    A deck with wicker furniture and a view of a lake and mountains.

    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.

    View all properties

    Find vacation rentals that suit your style

    Cabins

    Apartments

    Aparthotels

    Cottages

    Villas

    Condos

    Chalets

    Top Highland Falls Hotel Reviews

    The Thayer Hotel at West Point

    A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.

    Overlook Lodge at Bear Mountain

    A large, multi-story stone building with a prominent arched entrance and multiple windows.

    Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

    A buffet with labeled trays of turkey sausage and cookies.

    The Abbey Inn & Spa

    A conference room with a stone wall, a large arched window, and a television on the wall.

    Sleep Inn & Suites Monroe - Woodbury

    A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

    Comfort Suites Fishkill near Interstate 84

    A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

    Homewood Suites Stewart Airport

    A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

    Quality Inn & Suites Fishkill South near I-84

    A spacious living area with sofas, a fireplace, and artwork on the walls.

    Best Western Fishkill Inn & Suites

    A modern kitchen with a dining area, a staircase, and a door with a frosted glass panel.

    Parkway House Goshen Family-Friendly Bed & Breakfast

    A large, two-story house with a wrap-around porch and multiple chimneys.

    La Quinta Inn & Suites by Wyndham Middletown-Goshen

    A modern hotel building with a prominent sign, a covered entrance, and a parking area.

    Holiday Inn Express Hotel & Suites Chester by IHG

    A Holiday Inn Express hotel with a covered entrance, stone facade, and a clear sky.

    Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

    A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

    Inn on the Hudson

    A sign for the Inn on Hudson with pink flowers in the foreground.

    Find out more about Highland Falls

    Everything you need to know about Highland Falls vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Falls vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Falls vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Highland Falls vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Highland Falls. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Falls in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Highland Falls rentals

    At Expedia, we put the best Highland Falls vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Highland Falls rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Falls vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Falls. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Are there vacation rentals in Highland Falls?

    Yes, we have vacation rentals near top sights in Highland Falls, or you can choose a secluded option if you're looking for a relaxing stay. Highland Falls is known for its university setting and shopping. Make sure you have time to check out the waterfalls and soccer matches during your trip.

    What are some of the best vacation rentals that Highland Falls has to offer?

    Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Highland Falls is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

    How many vacation rentals are there in Highland Falls?

    Expedia has 22 vacation rentals for your stay in Highland Falls.

    What can I see and do in Highland Falls?

    Cultural attractions to visit include West Point Museum and United States Military Academy. Other places in town to visit include Bear Mountain State Park and Harriman State Park.

    What are vacation rentals like in Highland Falls?

    Vacation rentals are privately owned accommodations you can book for a short or long stay in Highland Falls. Vacation rentals feature extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.

    Explore a world of travel with Expedia