Photo by 💋Priscilla 💋

Highland Falls Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Highland Falls

Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
The price is ￥28,257
￥46,099 total
includes taxes & fees
Oct 27 - Oct 28
Fabulous 3bdrm Home w/parking!
Walk to WP Gate + Free Parking!
Exterior
Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (19)
"Great property and the hosts were very communicative."
The price is ￥25,431
￥41,611 total
includes taxes & fees
Oct 15 - Oct 16
Walk to WP Gate + Free Parking!
Home: 2 Mi to Thayer Gate at U.s. Military Academy
House (4 Bedrooms) | Interior
Home: 2 Mi to Thayer Gate at U.s. Military Academy
3.0 star property
Home: 2 Mi to Thayer Gate at U.s. Military Academy
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is ￥28,424
￥45,838 total
includes taxes & fees
Oct 28 - Oct 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (39)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is ￥39,158
￥49,941 total
includes taxes & fees
Nov 3 - Nov 4
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (26)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is ￥16,480
￥26,611 total
includes taxes & fees
Oct 15 - Oct 16
Cabin in the heart of the Hudson Valley, Cabin 2
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
10.0 out of 10, Exceptional, (194)
"Wonderful place to rest and recharge."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (42)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Chestnut on Willow Lake
Dining tables
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is ￥60,476
￥87,956 total
includes taxes & fees
Oct 15 - Oct 16
Chestnut on Willow Lake
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Hickory on Willow Lake
Children's area
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is ￥64,256
￥92,798 total
includes taxes & fees
Oct 15 - Oct 16
Hickory on Willow Lake
Rustic Cabin in Fishkill!
Exterior
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is ￥34,471
￥54,588 total
includes taxes & fees
Nov 1 - Nov 2
Rustic Cabin in Fishkill!
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Exterior
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
The Perfect Essential Getaway!
Interior
The Perfect Essential Getaway!
9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is ￥139,851
￥192,755 total
includes taxes & fees
Oct 15 - Oct 16
The Perfect Essential Getaway!
The Woodbury Cottage
Property grounds
The Woodbury Cottage
9.0 out of 10, Wonderful, (26)
"A cozy place to stay. "
The Woodbury Cottage
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Outdoor banquet area
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
8.8 out of 10, Excellent, (5)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is ￥126,848
￥205,966 total
includes taxes & fees
Oct 16 - Oct 17
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Large,Cozy,Bright Apartment, Business Themed.
Interior
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (14)
"Very cozy stay with responsive host"
The price is ￥61,232
￥102,335 total
includes taxes & fees
Oct 15 - Oct 16
Large,Cozy,Bright Apartment, Business Themed.
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Exterior
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Grant - A Tranquil One Bedroom Steps from River
Smart TV
Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (34)
"My partner and I came for a gathering of friends and family invthe area. It was the perfect place for us to get away and rest."
The price is ￥16,329
￥38,825 total
includes taxes & fees
Oct 21 - Oct 22
Grant - A Tranquil One Bedroom Steps from River
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Falls Hotel Reviews

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Close EV charging and parking. Staff was friendly and helpful."
Michael 1-night trip
Posted 12 hours ago
Hampton Inn & Suites Mahwah

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 vacation rentals in Highland Falls?

Yes, we have vacation rentals near top sights in Highland Falls, or you can choose a 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 soccer matches during your trip.

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

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This vacation home rental outside of Highland Falls is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Highland Falls?

Expedia has 20 vacation 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. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

What are vacation rentals like in Highland Falls?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Highland Falls. Vacation rentals feature extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.