Holiday rentals in Highland Falls

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Popular amenities for Highland Falls holiday rentals

Other great holiday rentals in Highland Falls

Top guest favourite
Guest suite in Highland Falls
5 out of 5 average rating, 13 reviews

West Point 1 Bedroom River View Apt within Home

MatthewRating, 5 stars7 months ago
This was a great experience and the entire process was smooth and easy. Great communication by the owner and really enjoyed it!
Guest favourite
Home in Highland Falls
5 out of 5 average rating, 38 reviews

Highland Falls Home - 1/2 Mile to West Point

CharlesRating, 5 stars1 month ago
This house in Highland Falls, NY, was perfect for our visit to West Point Military Academy. The house has very nice front porch and back porch. The living room and dining room are nicely equipped. Kitchen is ready-to-use — including basic spices, olive oil, coffee, and coffee filters. Even some snacks tucked into the cabinets and bottled water in the refrigerator. Similarly, the bathrooms have ample towels and wash clothes, hand soap, body wash, and shampoo. Everything immaculately clean. The house is very well located in the small town — you can easily walk to a couple restaurants, or drive. Everything within 6 or 7 minutes. USMA is just down the road. Karen the host is super-responsive and was very accommodating when we needed to adjust our dates. With our family group this was a really convenient and sociable place to stay for our visit.
Top guest favourite
Home in Highland Falls
4.99 out of 5 average rating, 138 reviews

Hudson Valley Farmhouse

JulieRating, 5 stars2 months ago
Kevin was a fantastic host and super responsive. Although we were in the area for a very sad funeral of a family member, the beautiful house and lovely surroundings were a welcome and peaceful respite. The furniture was very stylish and comfortable and the kitchen was fully equipped and well stocked as we often prepared our meals at home. Everything was extremely clean. We’ll definitely return!
Flat in Highland Falls
4.82 out of 5 average rating, 55 reviews

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

MandyRating, 5 stars3 weeks ago
Joe came through for us when a previously booked AirBnB cancelled last minute! We had a special event and were in a bind. We were concerned about fitting everyone in our party (4 adults) - with only one bedroom and two smaller sleeper sofas. Joe was very honest that it might be tight and offered an air mattress just in case. It worked out perfectly! The neighborhood is very close to some great restaurants and if you are staying to attend anything at West Point, it’s super convenient! The place is on the smaller side but perfect for a couple or a family with smaller kids. Would stay there again! Thank you Joe!
Top guest favourite
Home in Highland Falls
4.96 out of 5 average rating, 106 reviews

Ultimate Walking Access to Thayer Gate USMA

Rebecca LynnRating, 5 stars1 month ago
This house was beyond our expectations. I am someone who thinks of all the details and packs everything imaginable, but Monika had thought of everything for us! From instructions to where to find a flashlight in case of a power outage to lightswitches that were labeled, we felt so taken care of. It felt more like staying at a friends house than a sterile rental. Highly recommend. Its easy to see why they have repeat customers
Top guest favourite
Home in Highland Falls
5 out of 5 average rating, 15 reviews

Old Grad House, 850ft from Thayer Gate

DonnaRating, 5 stars6 months ago
Great place to stay for an Army game weekend. Very convenient to Post and West Point decor made it fun and interesting. Very clean, comfortable and well appointed. Robert is very responsive and friendly.
Top guest favourite
Home in Highland Falls
4.99 out of 5 average rating, 168 reviews

Spacious, bright 5 bedroom house near West Point

KrisRating, 5 stars2 weeks ago
I stayed here with my family and we absolutely loved it. It had everything we needed and more. We like to cook on our trips and the kitchen had everything we needed and more. Best stocked kitchenware I have ever found in all my travel. Host is thoughtful and proactive. Highly recommend
Guest favourite
Home in Highland Falls
4.96 out of 5 average rating, 85 reviews

West Point Mountain House

JasonRating, 5 stars2 weeks ago
The hosts were very responsive. It is a great house, exactly what we wanted and as advertised. There isn't much to do in the immediate area, but there are a few shops and restaurants in the town center. The house is situated in a back lot and shares an access driveway with the house closer to the street, but once you are at the house it is very private. The only issue we ran into is the three season porch hadn't been cleaned and was covered in pollen, so it wasn't very usable. This place is perfect for a large group that mostly wants to stay on site!

Quick stats about holiday rentals in Highland Falls

  • Total rentals

    60 properties

  • Nightly prices starting at

    ₹4,327 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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