Holiday rentals in Highland Falls

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highland Falls

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Farm stay in Fort Montgomery
Secluded mountain top horse property near W. Point
"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Enjoy fresh eggs every morning or vegetables from our organic garden (during season). Come, relax by the outdoor fire pit, fish or hike/explore the forest trails right out the front door.
10–17 JunIndividual Host,
£268 per night
4.94 out of 5 average rating, 196 reviews
Guest favourite
Cottage in Cortlandt
The Little Cottage in the Woods
The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests
19–26 JunIndividual Host,
£121 per night
4.99 out of 5 average rating, 157 reviews
Superhost
Flat in Highland Falls
Stay in the Heart of West Point! Walk to Academy
Enjoy this huge private 2 bedroom apartment on Main Street in the heartbeat of Highland Falls and walk just 3 mins to the Military Academy. At this perfect West Point getaway you'll find the best hiking, boating, swimming, fishing & golf this central location has to offer with a short drive to Bear Mountain State Park and ZOO, Woodbury Commons Outlet, Storm King Art Center, Eisenhower Theater and Legoland!! Perfect place to kick back and relax after an Army football game or day of hiking!
17–24 NovProfessional Host,
£245 per night
4.82 out of 5 average rating, 262 reviews

Popular amenities for Highland Falls holiday rentals

Stay near Highland Falls's top sights

The Thayer Hotel15 locals recommend
West Point Academy60 locals recommend
The Park11 locals recommend
Andy's11 locals recommend
American Burrito3 locals recommend
Schade's6 locals recommend

Other great holiday rentals in Highland Falls

Guest favourite
Home in Highland Falls
Grad owned cozy 5 bd home right outside West Point
2–9 AugIndividual Host,
£311 per night
4.96 out of 5 average rating, 53 reviews
Guest favourite
Home in Highland Falls
GRAD MOM House Walk to WP King 2 Queen
25 Jul – 1 AugIndividual Host,
£422 per night
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Highland Falls
Modern West Point Retreat: 3BR, 2BA w/Hot Tub fire
1–8 FebIndividual Host,
£471 per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Highland Falls
House on the Babbling Brook
8–13 AprIndividual Host,
£168 per night
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Highland Falls
West Point Mountain House
4–11 JunIndividual Host,
£550 per night
4.96 out of 5 average rating, 49 reviews
Guest favourite
Guest suite in Highland Falls
Quiet, Cozy, Private Suite ~1/2 mile to West Point
17–24 MayIndividual Host,
£196 per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Flat in Highland Falls
Lovely 2nd FL Apt Walking Distance to West Point!
1–8 FebIndividual Host,
£167 per night
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Highland Falls
Highland Falls Home - 1/2 Mile to West Point
20–27 JanIndividual Host,
£245 per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Highland Falls
Cozy House 3 Blocks From West Pt
15–22 JulIndividual Host,
£460 per night
5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Highland Falls
Bear Mountain, Westpoint, & Hikers Retreat
8–15 JulIndividual Host,
£149 per night
5.0 out of 5 average rating, 67 reviews
Guest favourite
Home in Highland Falls
Best Location to West Point, Beautiful Farmhouse
27 Mar – 3 AprIndividual Host,
£377 per night
4.96 out of 5 average rating, 89 reviews
Guest favourite
Home in Highland Falls
Modern Farmhouse Near West Point
31 Jan – 7 FebIndividual Host,
£291 per night
4.78 out of 5 average rating, 18 reviews

Quick stats about holiday rentals in Highland Falls

Total rentals

50 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.3K reviews

Nightly prices starting at

£39 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Highland Falls