A lake surrounded by hills with autumn foliage.

Highland Falls Holiday Rentals

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Check prices for these dates

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

Our top choices for Highland Falls holiday 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
9.4 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.
The price is HK$902
HK$2,408 total
includes taxes & fees
4 Oct - 5 Oct
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, (13 reviews)
"A very quiet cul de sac and a babbling brook in the back yard which was absolutely soothing. Street parking was tight but there was a small parking lot available close by. Beds were comfortable (pillows need upgraded though). Kitchen could use a few more plates and bowls. I cooked for 7 people. Towels (rough). A few upgrades and this place would be a five."
United States
Tina
The price is HK$1,067
HK$3,280 total
includes taxes & fees
6 Oct - 7 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

3. 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.
The price is HK$1,177
HK$3,680 total
includes taxes & fees
6 Oct - 7 Oct
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.

4. 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.
The price is HK$1,028
HK$3,463 total
includes taxes & fees
6 Oct - 7 Oct
3BR Near West Point | Coffee Bar | Sleeps 6
Living area

5. 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.
The price is HK$1,053
HK$1,905 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

6. 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.
The price is HK$1,123
HK$3,568 total
includes taxes & fees
6 Oct - 7 Oct
Local Artist Inspired | Walk to WestPoint + King Bed
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.
The price is HK$1,953
HK$3,185 total
includes taxes & fees
28 Oct - 29 Oct
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A blue house with a white porch, a welcome sign, and a mailbox.

8. 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.
The price is HK$1,099
HK$3,846 total
includes taxes & fees
6 Oct - 7 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
A living room with a leather sofa, a round coffee table, a bench, and a ceiling fan.

9. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
Highland Falls
10.0 out of 10, Exceptional, (38 reviews)
"There were no surprises and the whole experience worked great. Highly recommend."
United States
Dave D.
The price is HK$1,718
HK$4,995 total
includes taxes & fees
4 Oct - 5 Oct
Updated Home w/ Patio Half Mile to West Point
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.
The price is HK$2,068
HK$3,616 total
includes taxes & fees
28 Oct - 29 Oct
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.

11. 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.
The price is HK$2,257
HK$3,759 total
includes taxes & fees
28 Oct - 29 Oct
Fabulous 3bdrm Home w/parking!
A wooden coffee table with two decorative planters in a living room.

12. 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.
The price is HK$2,159
HK$3,450 total
includes taxes & fees
28 Oct - 29 Oct
Walk to WP Gate + Free Parking!
A living room with a leather sofa, a round coffee table, a bench, and a ceiling fan.

13. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is HK$2,142
HK$4,942 total
includes taxes & fees
4 Oct - 5 Oct
Updated Home w/ Patio Half Mile to West Point
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

14. 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.
The price is HK$3,915
HK$6,502 total
includes taxes & fees
13 Oct - 14 Oct
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,554
HK$2,595 total
includes taxes & fees
6 Oct - 7 Oct
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, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is HK$1,765
HK$3,294 total
includes taxes & fees
6 Oct - 7 Oct
Contemporary Cozy Cottage
Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

17. 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, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,239
HK$3,725 total
includes taxes & fees
6 Oct - 7 Oct
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A deck with Adirondack chairs, a fire pit, and a grill.

18. 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
The price is HK$1,781
HK$3,513 total
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A living room with a fireplace, a painting, shelves with decorative items, and a television.

19. 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.
The price is HK$1,059
HK$2,308 total
includes taxes & fees
5 Oct - 6 Oct
Grant - A Tranquil One Bedroom Steps from River
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

20. 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 traveller
The price is HK$564
HK$638 total
includes taxes & fees
26 Oct - 27 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"It’s got a great view -but the property is getting old and need some attention!"
Sean 1-night trip
Posted 5 hours ago
Inn on the Hudson

Find out more about Highland Falls

Search for holiday rentals in Highland Falls on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Falls using one of the methods below:

  • View our selection of featured holiday rentals in Highland Falls
  • Use the map to find apartments and other holiday homes in the Highland Falls neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Falls while they last

Look no further and take a look at our great range of rental properties in Highland Falls!

Frequently asked questions

Are there holiday rentals in Highland Falls?

Yes, there are holiday rentals close to the most popular sights in Highland Falls, or you can select a more 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 football matches during your trip.

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

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

How many holiday rentals are there in Highland Falls?

Expedia has 22 holiday 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 holiday rentals like in Highland Falls?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Falls. Holiday rentals feature amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips or small group gatherings.