A lake surrounded by hills with autumn foliage.

Highland Falls Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Highland Falls vacation rentals

Coffee/tea maker, fridge, oven, stovetop

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,676
￥49,836 total
includes taxes & fees
Jul 26 - Jul 27
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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 ￥20,300
￥65,520 total
includes taxes & fees
Jul 23 - Jul 24
House on the Babbling Brook- Quiet 2BR + 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 ￥25,407
￥44,117 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 1-bedroom retreat minutes from West Point!
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 ￥21,939
￥77,768 total
includes taxes & fees
Jul 22 - Jul 23
3BR West Point Retreat-3min to Back Gate+ King Bed
Coffee/tea maker, fridge, microwave, oven

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 ￥35,322
￥58,693 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
The price is ￥34,093
￥57,650 total
includes taxes & fees
Jul 23 - Jul 24
Walk to WP Gate + Free Parking!
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
The price is ￥29,947
￥55,962 total
includes taxes & fees
Jul 23 - Jul 24
Fabulous 3bdrm Home w/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 ￥30,254
￥57,460 total
includes taxes & fees
Jul 22 - Jul 23
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥32,155
￥54,098 total
includes taxes & fees
Jul 23 - Jul 24
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥30,263
￥79,460 total
includes taxes & fees
Jul 22 - Jul 23
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Outdoor spa tub

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥31,689
￥65,077 total
includes taxes & fees
Jul 22 - Jul 23
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is ￥21,924
￥46,481 total
includes taxes & fees
Aug 17 - Aug 18
Grant - A Tranquil One Bedroom Steps from River
Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥36,565
￥68,588 total
includes taxes & fees
Aug 2 - Aug 3
Contemporary Cozy Cottage
1 bedroom, WiFi (free)

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥17,840
￥20,181 total
includes taxes & fees
Aug 3 - Aug 4
2 Queen Beds | Non-Smoking, Kitchen
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is ￥20,950
￥32,422 total
includes taxes & fees
Aug 6 - Aug 7
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior

1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Nice place to stay"
United States
Anonymous traveler
The price is ￥16,218
￥18,752 total
includes taxes & fees
Aug 3 - Aug 4
1 Queen Bed | Non-Smoking, Kitchen
Terrace/patio

River Views & Deck | River Suite on Washington

River Views & Deck | River Suite on Washington
Newburgh
The price is ￥21,256
￥65,758 total
includes taxes & fees
Jul 22 - Jul 23
River Views & Deck | River Suite on Washington
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is ￥17,052
￥32,150 total
includes taxes & fees
Aug 19 - Aug 20
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥34,907
￥65,945 total
includes taxes & fees
Aug 3 - Aug 4
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (71 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is ￥28,420
￥54,674 total
includes taxes & fees
Jul 28 - Jul 29
Cozy country efficiency in the Hudson Valley
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"The room was clean; small refrigerator; bathroom vanity not in the bathroom; ice only available on the ground floor."
Sally 1-night trip
Posted 1 hour ago
Spark by Hilton Fishkill

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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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?

House on the Babbling Brook- Quiet 2BR + King Bed!: This highly rated vacation home rental in Highland Falls offers a balcony, a barbecue grill, 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 vacation rentals are there in Highland Falls?

Expedia has 21 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.