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Highland Falls Holiday Rentals

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Holiday Rentals in Highland Falls

Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
9.2 out of 10, Wonderful, (15)
"The property is walkable to everything Highland Falls and West Point. It is in an older building, so the stairs maybe be a little steep for someone elderly or who has a hard time negotiating stairs. The host was amazing, communicating frequently and accurately. Would recommend to anyone!"
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$460
includes taxes & fees
10 Jun - 11 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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Cottage at Millpond Falls - A Romantic and Luxurious Escape
10.0 out of 10, Exceptional, (126)
"Cottage is super clean, lots of extras i dont usually see, snacks, drinks etc. Water fall is spectacular,albeit loud lol bed and bedding was very comfortable Owners very nice. Great stay."
Cottage at Millpond Falls - A Romantic and Luxurious Escape
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (37)
"This end of the cul-de-sac accommodation is attached to the owners home. With a beautiful view from the attached patio I was happy to leave my screen door open any time I was there. The bedding and bed were comfortable and clean. The kitchen was fairly well stocked with cooking tools, plates, cups, coffee maker, toaster oven, dishwasher, towels, a fridge (bigger than a mini) with a filtered water dispenser. I will remember to bring my own tea bags if I stay again. The small bathroom was perfect...
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (116)
"This is our second visited and we are still in love with the Lake House!"
Lakefront Luxury on Greenwood Lake
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (62)
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (40)
"This was a perfect hideaway located 15 minutes from Beacon where the wedding was. It was reasonably priced and had so many cute accents. The host was on top of all the details and very nice in person. Would definitely recommend. The only thing I would say just for an fyi it’s better for a couple as it’s a full size bed. I went with my teen daughter and it was too small for both of us in the bed so we alternated the couch. Not a minus at all but more an fyi. Thanks so much for hosting us."
The price is NZ$349
includes taxes & fees
9 Jun - 10 Jun
Cozy country efficiency in the Hudson Valley
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, (168)
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, (4)
"we were able to have all 3 of our children, with 2 of their spouses and bridal party for my daughter stay with us for the weekend. There were plenty of things to entertain during downtime. Rooms were comfortable and location was convenient to wedding activities."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Newly Renovated Gorgeous Home in Goshen
9.8 out of 10, Exceptional, (32)
"With extended family in this area, we have stayed in several local rentals while visiting relatives and this one is near the top. The home is newly renovated and clean, the property is beautiful, and the area is very peaceful. This is a great find and I would highly recommend."
Newly Renovated Gorgeous Home in Goshen
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is NZ$517
includes taxes & fees
17 Jun - 18 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Hudson Valley Newburgh -Remodel Lrg Apt
5.0 out of 10, (2)
"The pictures in this listing completely misrepresented the neighborhood. We only spent about an hour in the VRBO but didn't feel safe there for several reasons. First of all, the room wasn't secure because it was opened up to the neighborhood through the upper floor that let out to the fire escape. Second of all there were large groups of people in the streets having block parties that made us feel like our rental car wasn't safe from vandalism or burglary. The last straw was when we talked to a...
Hudson Valley Newburgh -Remodel Lrg Apt
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$264
includes taxes & fees
9 Jun - 10 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
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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.

Other types of properties in Highland Falls you may be interested in

FairBridge Inn & Suites at West Point
2.0 star property
6.2 out of 10, (620)
"Nice friendly staff. Easy check in. Welcoming. Renovated rooms and bathrooms. Great rooms!"
The price is NZ$234
includes taxes & fees
19 Jun - 20 Jun
FairBridge Inn & Suites at West Point
West Point Motel
2.5 star property
8.2 out of 10, Very good, (487)
"Good Place to stay"
The price is NZ$293
includes taxes & fees
6 Jun - 7 Jun
West Point Motel
West Gate Inn Nyack
3.0 star property
7.4 out of 10, Good, (998)
"Very friendly staff. Very clean"
The price is NZ$189
includes taxes & fees
16 Jun - 17 Jun
West Gate Inn Nyack
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highland Falls holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highland Falls. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highland Falls. Seeing all the best attractions is bound to make you fall in love with Highland Falls. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highland Falls short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Highland Falls?

Expedia has 9 holiday rentals for your stay in Highland Falls.

What can I see and do in Highland Falls?

Cultural attractions include West Point Museum and United States Military Academy, whereas Bear Mountain State Park and Harriman State Park are a couple of picturesque spots to enjoy the outdoors. 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.

Recent reviews of Highland Falls properties
Expedia verified reviews