A lake surrounded by hills with autumn foliage.

Highland Falls Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Highland Falls vacation rentals

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

1. 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, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$379 nightly
The price is $405
Oct 1 - Oct 2
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$299 nightly
The price is $307
Oct 1 - Oct 2
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$227 nightly
The price is $251
Oct 28 - Oct 29
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$443 nightly
The price is $455
Oct 6 - Oct 7
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.

5. 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.
$457 nightly
The price is $469
Oct 6 - Oct 7
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A hallway with a wooden door, a black table with a sign, and large green plants.

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

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
$430 nightly
The price is $441
Oct 6 - Oct 7
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
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.
$244 nightly
The price is $271
Oct 1 - Oct 2
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A wooden coffee table with two decorative planters in a living room.

8. 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.
$225 nightly
The price is $249
Oct 1 - Oct 2
Total with taxes and fees
Walk to WP Gate + Free Parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

9. 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.
$288 nightly
The price is $329
Oct 1 - Oct 2
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

10. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
$426 nightly
The price is $479
Oct 28 - Oct 29
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

11. Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Highland Falls
9.6 out of 10, Exceptional, (36 reviews)
"Good location and had a great stay!"
United States
James M.
$673 nightly
The price is $829
Oct 11 - Oct 12
Total with taxes and fees
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A house with a view of a bridge and mountains.

12. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 6 - Oct 7
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.

13. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
$367 nightly
The price is $420
Oct 4 - Oct 5
Total with taxes and fees
Contemporary Cozy Cottage
A living room with a fireplace, a painting, shelves with decorative items, and a television.

14. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 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.
$260 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A deck with Adirondack chairs, a fire pit, and a grill.

15. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$376 nightly
The price is $444
Oct 6 - Oct 7
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

16. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$72 nightly
The price is $81
Oct 5 - Oct 6
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
$80 nightly
The price is $92
Oct 26 - Oct 27
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

18. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
$191 nightly
The price is $226
Oct 1 - Oct 2
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

19. 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.
$653 nightly
The price is $721
Oct 7 - Oct 8
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

20. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$247 nightly
The price is $279
Oct 1 - Oct 2
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

10/10 Excellent
"Big clean room! Bed is super comfy! Would definitely return when in the area."
Alyssa 1-night trip
Posted less than an hour ago
Comfort Suites Fishkill near Interstate 84

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 $92 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.