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Highland Falls Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Highland Falls

Our top choices for Highland Falls vacation rentals

Walk to WP Gate + Free Parking!
Exterior

Walk to WP Gate + Free Parking!

9.8 out of 10, Exceptional, (16)
"Great property and the hosts were very communicative."
The price is ￥21,079
￥34,898 total
includes taxes & fees
Sep 25 - Sep 26
Walk to WP Gate + Free Parking!
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 ￥22,489
￥39,168 total
includes taxes & fees
Sep 25 - Sep 26
Fabulous 3bdrm Home w/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 ￥27,751
￥45,421 total
includes taxes & fees
Sep 30 - Oct 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.
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, (193)
"We loved the house, it was very quiet, the view of the lake was beautiful (even though it was rainy and cloudy). The decoration was really nice and it felt super cozy. The host was also very responsive. "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
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, (35)
"Great place for a quiet stay"
The price is ￥38,231
￥48,759 total
includes taxes & fees
Oct 12 - Oct 13
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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

9.8 out of 10, Exceptional, (7)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"Fortunate to have found the time to spend a long weekend by the lake. Just the right remedy for our usual fast-paced schedules. Caught a beautiful sunset the first evening but every day was just as enjoyable."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (22)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ￥26,570
￥70,635 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"This property has exactly what we were looking for to spend a long weekend and create new memories. The welcoming atmosphere and breathtaking views offer a unique experience. Jones was easily accessible to respond to any questions. We will certainly come and definitely recommend this property to family and friends. "
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
Outdoor dining

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
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.
A luxurious stay.
Smart TV

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is ￥18,599
￥42,583 total
includes taxes & fees
Sep 30 - Oct 1
A luxurious stay.
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 ￥40,593
￥61,576 total
includes taxes & fees
Sep 30 - Oct 1
Rustic Cabin in Fishkill!
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Outdoor dining

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

10.0 out of 10, Exceptional, (2)
"Beautiful home, on a quiet street. Ample view from the living room, kitchen and deck/dock. We loved have a little private beach area for my daughter. The game room was such a fun bonus!! We will definitely be back !! "
The price is ￥29,800
￥68,593 total
includes taxes & fees
Sep 29 - Sep 30
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Greenwood Lake Lakefront Luxury
Property grounds

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (142)
"We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!"
Greenwood Lake Lakefront Luxury
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Outdoor dining

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

10.0 out of 10, Exceptional, (5)
"This condo is located very close to the Garrison train station. It has been designed so that you are never disturbed by the sound of the trains. Really soundproof! There is a beautiful view of West Point across the Hudson River from the balcony and other windows. The kitchen and 2 1/2 bathrooms are modern and well equipped. Matt, the host, has thought of everything when it comes to making his guests feel comfort and st home. The beds were extra comfy and both bedrooms were quite spacious....
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
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 ￥59,044
￥85,874 total
includes taxes & fees
Sep 25 - Sep 26
Chestnut on Willow Lake
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is ￥59,782
￥99,911 total
includes taxes & fees
Sep 26 - Sep 27
Large,Cozy,Bright Apartment, Business Themed.
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Check in girl was nice and friendly."
Gretchen 1-night trip
Posted 18 hours ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Highland Falls

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!

Explore a world of travel with Expedia

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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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Highland Falls offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Highland Falls?

Expedia has 19 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.