A lake surrounded by hills with autumn foliage.

Highland Falls Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Highland Falls holiday rentals

Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$1,223
HK$3,361 total
includes taxes & fees
8 Jul - 9 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, microwave, oven, stovetop

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is HK$1,987
HK$3,200 total
includes taxes & fees
7 Jul - 8 Jul
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"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 HK$2,388
HK$4,017 total
includes taxes & fees
7 Jul - 8 Jul
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is HK$1,349
HK$4,029 total
includes taxes & fees
6 Jul - 7 Jul
3BR West Point Retreat-3min to Back Gate+ King Bed
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$1,219
HK$2,073 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 1-bedroom retreat minutes from West Point!
3 bedrooms, desk, iron/ironing board, travel cot

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (17 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is HK$1,130
HK$3,543 total
includes taxes & fees
6 Jul - 7 Jul
Local Artist Inspired | Walk to WestPoint + King Bed
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$2,322
HK$3,840 total
includes taxes & fees
15 Jul - 16 Jul
Fabulous 3bdrm Home w/parking!
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is HK$2,487
HK$3,845 total
includes taxes & fees
8 Jul - 9 Jul
Walk to WP Gate + Free Parking!
Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is HK$1,663
HK$4,052 total
includes taxes & fees
19 Jul - 20 Jul
Hudson Valley Retreat w/ Pool Near Greenwood Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,325
HK$2,196 total
includes taxes & fees
13 Jul - 14 Jul
Cabin in the Heart of the Hudson Valley, Cabin 1
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,326
HK$2,214 total
includes taxes & fees
6 Jul - 7 Jul
Cabin in the heart of the Hudson Valley, Cabin 3
Private kitchen

2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (2 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is HK$1,482
HK$1,908 total
includes taxes & fees
8 Jul - 9 Jul
2-bedroom apartment in excellent Newburgh with AC and charm
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is HK$2,545
HK$3,607 total
includes taxes & fees
13 Jul - 14 Jul
Charming Cabin in Fishkill!
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,765
HK$3,292 total
includes taxes & fees
9 Jul - 10 Jul
Contemporary Cozy Cottage
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is HK$2,580
HK$4,290 total
includes taxes & fees
5 Jul - 6 Jul
Luxury 3BR with King Beds in Montgomery Village
TV, fireplace, DVD player

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is HK$1,294
HK$4,100 total
includes taxes & fees
19 Jul - 20 Jul
Hudson Valley Retreat w/ Pool Near Greenwood Lake
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (15 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,765
HK$3,306 total
includes taxes & fees
9 Jul - 10 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, oven, stovetop, dishwasher

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is HK$2,000
HK$4,303 total
includes taxes & fees
19 Jul - 20 Jul
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Interior

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is HK$1,906
HK$2,541 total
includes taxes & fees
9 Jul - 10 Jul
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Smart TV, fireplace, video games, DVD player

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is HK$4,228
HK$7,625 total
includes taxes & fees
6 Jul - 7 Jul
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Rooms were clean and A/C worked well. Lots of water pressure in the shower. Friendly staff."
Kevin 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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:

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  • 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 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?

House on the Babbling Brook- Quiet 2BR + King Bed!: This highly rated holiday home rental in Highland Falls offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Highland Falls?

Expedia has 22 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. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

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.