A lake surrounded by hills with autumn foliage.

Highland Falls Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Highland Falls vacation rentals

1. 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.
$229 nightly
The price is $254
Sep 2 - Sep 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

2. 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.
$297 nightly
The price is $327
Sep 1 - Sep 2
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

3. 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.
$289 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

4. 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.
$360 nightly
The price is $402
Sep 1 - Sep 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.

5. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$265 nightly
The price is $293
Sep 2 - Sep 3
Total with taxes and fees
Walk to WP Gate + Free Parking!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

6. 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.
$474 nightly
The price is $584
Sep 1 - Sep 2
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.

7. 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, (141 reviews)
"We had a great stay!!"
United States
Jasmine
$284 nightly
The price is $335
Sep 1 - Sep 2
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A deck with Adirondack chairs, a fire pit, and a grill.

8. 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, (13 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$355 nightly
The price is $419
Sep 9 - Sep 10
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

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

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$436 nightly
The price is $481
Sep 1 - Sep 2
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

10. 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.
$400 nightly
The price is $458
Sep 28 - Sep 29
Total with taxes and fees
Contemporary Cozy Cottage
A living room with a fireplace, a painting, shelves with decorative items, and a television.

11. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 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.
$257 nightly
The price is $291
Sep 7 - Sep 8
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
$74 nightly
The price is $86
Oct 1 - Oct 2
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.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
$565 nightly
The price is $624
Sep 8 - Sep 9
Total with taxes and fees
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A deck with wicker furniture, a bench, and a table.

14. River Views & Deck | River Suite on Washington

River Views & Deck | River Suite on Washington
Newburgh
$361 nightly
The price is $424
Sep 2 - Sep 3
Total with taxes and fees
River Views & Deck | River Suite on Washington
An outdoor patio area with a covered seating area, a pool, and potted plants.

15. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (74 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
$298 nightly
The price is $345
Sep 1 - Sep 2
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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
$74 nightly
The price is $83
Sep 16 - Sep 17
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

17. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
$291 nightly
The price is $333
Sep 2 - Sep 3
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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
$193 nightly
The price is $228
Sep 2 - Sep 3
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

19. 2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
$216 nightly
The price is $244
Sep 7 - Sep 8
Total with taxes and fees
2-bedroom apartment in excellent Newburgh with AC and charm
A wooden cabin with large windows, a wooden bench, and a view of the forest.

20. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Sep 7 - Sep 8
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

8/10 Good
"The breakfast was really good! The staff were very kind and accommodating. The room was clean but not impeccable. It was, however, dark. No random flashing lights or blinking alarms. And that's pretty wonderful."
Katherine 3-night trip
Posted less than an hour ago
Hyatt Place Poughkeepsie / Hudson Valley

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 $86 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Highland Falls offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Highland Falls?

Expedia has 17 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.