Highland Falls Vacation Rentals

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Make Highland Falls your next getaway

Highland Falls, NY vacation rentals

Explore Highland Falls house rentals, and more

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House rentals

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Highland Falls vacation rentals for every getaway

Popular
Internet Lake view Waterfront
Home: 2 Mi to Thayer Gate at U.S. Military Academy

Home: 2 Mi to Thayer Gate at U.S. Military Academy

House in Highland Falls

$724 avg / night

5.0 (3)
Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point

House in Highland Falls

$528 avg / night

5.0 (5)
Charming Highland Falls Home < 2 Mi to West Point!

Charming Highland Falls Home < 2 Mi to West Point!

House in Highland Falls

$570 avg / night

View homes on map

Listings nearby Highland Falls

'The Glabin’: Garrison Gem w/ Hot Tub & Fire Pit

'The Glabin’: Garrison Gem w/ Hot Tub & Fire Pit

House in Philipstown

$693 avg / night

5.0 (4)
Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!

House in Cornwall On Hudson

$643 avg / night

4.8 (5)
Historic 1800s Cornwall-On-Hudson Cottage!

Historic 1800s Cornwall-On-Hudson Cottage!

Cottage in Cornwall On Hudson

$620 avg / night

5.0 (9)
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

Apartment in Newburgh

$247 avg / night

Vacation rentals near Highland Falls

Explore more vacation rental amenities in Highland Falls

A/C
Washer/dryer
Ping-pong table
Kayaks
Mountain view
Snowbird-friendly

Recent Highland Falls vacation rental reviews

The property was clean and spacious. Convenient to West Point and Bear Mountain. Very happy with our experience.
Scott . | Nov 2025
Great stay in a lovely home. Well furnished and a complete kitchen. Loved the West Point decor!
Jill . | Oct 2025
Great location and responsive host. The house is very clean! Our West Point cadet who had just undergone SAMI (Saturday morning inspection) even commented on how clean it was!
Cindy . | Aug 2025
OVERALL THE HOME WAS VERY INVITING, AND COMFORTABLE. VERY CLEAN AND NICELY DECORATED. WE WOULD STAY AGAIN IN THE FUTURE. THANKS AGAIN.
Timothy . | Jun 2025
Highland Falls Frequently Asked Questions

Yes. 14 of our Highland Falls vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Highland Falls vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Highland Falls team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Highland Falls, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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