Highland Falls Holiday Rentals

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Our top choices for Highland Falls holiday rentals

10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$325
includes taxes & fees
28 Jan - 29 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is NZ$630
includes taxes & fees
5 Jan - 6 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is NZ$776
includes taxes & fees
14 Jan - 15 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$456
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is NZ$481
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"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 NZ$644
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely 3BR Home with parking-Walk to WP Gate!
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is NZ$675
includes taxes & fees
5 Jan - 6 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed
2.0 star property
Cozy Modern Stay - Walk to West Point & Main St!

Holiday Home in Highland Falls

Fabulous 3bdrm Home w/parking!
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is NZ$591
includes taxes & fees
7 Jan - 8 Jan 2026
Fabulous 3bdrm Home w/parking!

Apartment in Highland Falls

Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (21)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is NZ$561
includes taxes & fees
7 Jan - 8 Jan 2026
Walk to WP Gate + Free Parking!

Holiday Home in Highland Falls

Luxury House Near West Point
2.0 star property
The price is NZ$550
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury House Near West Point

Holiday Home in Highland Falls

Luxury Townhouse Near West Point
2.0 star property
The price is NZ$632
includes taxes & fees
29 Dec - 30 Dec
Luxury Townhouse Near West Point

Holiday Home in Highland Falls

Luxury home near West Point
2.0 star property
The price is NZ$865
includes taxes & fees
11 Jan - 12 Jan 2026
Luxury home near West Point
10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
United States
Alain C.
The price is NZ$1,787
includes taxes & fees
8 Jan - 9 Jan 2026
Room for Everyone: Spacious 6BR West Point Retreat

Holiday Home in Highland Falls

Luxury Home Near West Point
2.0 star property
The price is NZ$873
includes taxes & fees
10 Jan - 11 Jan 2026
Luxury Home Near West Point
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is NZ$478
includes taxes & fees
11 Jan - 12 Jan 2026
Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is NZ$606
includes taxes & fees
29 Dec - 30 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is NZ$412
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$264
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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

Find out more about Highland Falls

Everything you need to know about Highland Falls holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Falls holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland Falls holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland Falls holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Falls holiday rentals we have selected for you start as low as NZ$264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland Falls rentals

At Expedia, we put the best Highland Falls holiday 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 holiday.

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 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?

Fabulous 3bdrm Home w/parking!: This highly rated holiday home rental in Highland Falls offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Highland Falls?

Expedia has 26 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.