A lake surrounded by hills with autumn foliage.

Highland Falls Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Highland Falls vacation rentals

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

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$275 nightly
The price is $282
Nov 2 - Nov 3
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

2. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Host was available and communicated very well. The house was very clean too."
United States
Erika
$378 nightly
The price is $404
Oct 30 - Oct 31
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$202 nightly
The price is $223
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A blue house with a white porch, a welcome sign, and a mailbox.

4. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
$419 nightly
The price is $479
Nov 3 - Nov 4
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$433 nightly
The price is $444
Nov 1 - Nov 2
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

6. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
$458 nightly
The price is $470
Nov 1 - Nov 2
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
$306 nightly
The price is $343
Nov 17 - Nov 18
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A hallway with a wooden door, a black table with a sign, and large green plants.

8. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
$437 nightly
The price is $449
Nov 1 - Nov 2
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A bedroom with a bed, bedside tables, a ceiling fan, a window with curtains, and a door leading to another room.

9. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
$297 nightly
The price is $333
Nov 2 - Nov 3
Total with taxes and fees
Mountain-View 2BR Steps from Thayer Gate
A room with a wooden floor, a white door with a number, and a window with blinds.

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

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$347 nightly
The price is $399
Nov 17 - Nov 18
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A room with a ceiling fan, a wooden floor, a black sofa, a wooden coffee table, and a TV mounted on the wall.

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
$320 nightly
The price is $359
Nov 2 - Nov 3
Total with taxes and fees
Perfect 2BR with Free Parking! Walk to West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

12. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
$359 nightly
The price is $402
Nov 2 - Nov 3
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A wooden coffee table with two decorative planters in a living room.

13. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$335 nightly
The price is $377
Nov 17 - Nov 18
Total with taxes and fees
Walk to WP Gate + Free Parking!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
$454 nightly
The price is $528
Nov 17 - Nov 18
Total with taxes and fees
Hudson Valley/West Point Retreat w/ parking!
A house with a view of a bridge and mountains.

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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (149 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Nov 2 - Nov 3
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

16. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
$367 nightly
The price is $420
Nov 1 - Nov 2
Total with taxes and fees
Contemporary Cozy Cottage
A deck with Adirondack chairs, a fire pit, and a grill.

17. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$375 nightly
The price is $443
Nov 9 - Nov 10
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A living room with a fireplace, a painting, shelves with decorative items, and a television.

18. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$331 nightly
The price is $374
Nov 3 - Nov 4
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
$79 nightly
The price is $91
Nov 23 - Nov 24
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

20. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
$594 nightly
The price is $655
Nov 1 - Nov 2
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
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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Top Highland Falls Hotel Reviews

West Gate Inn Nyack

West Gate Inn Nyack

8/10 Good
"This is good for a small visit or stay if you are alone. I honestly wouldn't have minded to stay here the full time but I left early because my girlfriend didn't feel safe. Other than that the staff was easy to talk to, the location is fair, and the room has its ups and downs but it's all around good."
Owen 3-night trip
Posted 7 hours ago
West Gate Inn Nyack

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 $91 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.

Explore a world of travel with Expedia

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.