Highland Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Highland vacation rentals

Terrace/patio

Apartment in Highland

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
10.0 out of 10, Exceptional, (1 review)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is ￥25,691
￥59,117 total
includes taxes & fees
Jan 25 - Jan 26
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Property grounds

Apartment in Highland

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location and stay"
United States
kareem e.
The price is ￥33,476
￥50,223 total
includes taxes & fees
Jan 26 - Jan 27
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥10,899
￥49,634 total
includes taxes & fees
Jan 26 - Jan 27
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

Apartment in Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
9.0 out of 10, Wonderful, (15 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥8,470
￥23,635 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Apartment with Sauna in Historic Stone Ridge
Interior

Vacation Home in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (31 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥9,498
￥36,098 total
includes taxes & fees
Jan 27 - Jan 28
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥11,678
￥40,142 total
includes taxes & fees
Jan 25 - Jan 26
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Interior

Vacation Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is ￥10,556
￥27,278 total
includes taxes & fees
Feb 2 - Feb 3
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is ￥8,470
￥25,192 total
includes taxes & fees
Jan 25 - Jan 26
Dream getaway apartment in the foot of Gunks Ridge
Terrace/patio

Chalet in Gardiner

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
10.0 out of 10, Exceptional, (8 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is ￥14,986
￥31,708 total
includes taxes & fees
Jan 26 - Jan 27
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ￥13,546
￥57,226 total
includes taxes & fees
Jan 27 - Jan 28
Local Artist Inspired | Walk to WestPoint + King Bed
Property grounds

Apartment in Rhinebeck Village

Private Studio Close to Downtown Rhinebeck
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is ￥12,999
￥36,942 total
includes taxes & fees
Jan 26 - Jan 27
Private Studio Close to Downtown Rhinebeck
Terrace/patio

Apartment in Kingston

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (27 reviews)
"Very clean very comfortable beds."
United States
Millgate F.
The price is ￥15,414
￥39,062 total
includes taxes & fees
Feb 2 - Feb 3
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Interior

Apartment in Beacon

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
10.0 out of 10, Exceptional, (46 reviews)
"Great place!"
United States
Sara B.
The price is ￥17,127
￥37,463 total
includes taxes & fees
Jan 25 - Jan 26
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Fireplace, books

Cottage in Kerhonkson

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is ￥12,380
￥29,102 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Exterior detail

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,127
￥35,851 total
includes taxes & fees
Jan 26 - Jan 27
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds

Apartment in Staatsburg

Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (44 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is ￥17,399
￥30,428 total
includes taxes & fees
Feb 1 - Feb 2
Mid-Century DJ’s Dream
Smart TV

Apartment in Kingston

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
9.4 out of 10, Exceptional, (22 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is ￥14,013
￥35,923 total
includes taxes & fees
Jan 27 - Jan 28
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Exterior detail

Vacation Home in New Paltz

Cozy private suite in the heart of beautiful Gardiner.
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is ￥18,077
￥37,508 total
includes taxes & fees
Jan 26 - Jan 27
Cozy private suite in the heart of beautiful Gardiner.
Interior

Apartment in Kingston

Stunning and Cozy loft apartment in kingston .
9.4 out of 10, Exceptional, (14 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is ￥18,217
￥34,354 total
includes taxes & fees
Jan 26 - Jan 27
Stunning and Cozy loft apartment in kingston .
Property grounds

Apartment in Hyde Park

Hudson Valley Farm Getaway- West/Llama Lover Lane
9.8 out of 10, Exceptional, (6 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is ￥24,834
￥32,410 total
includes taxes & fees
Jan 27 - Jan 28
Hudson Valley Farm Getaway- West/Llama Lover Lane
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 Hotel Reviews

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent
"The staff was very friendly and helpful. We would definitely stay again."
Alicia 1-night trip
Posted 2 days ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Highland!

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Frequently asked questions

Can I find vacation rentals in Highland?

Yes, we offer vacation rentals close to the most popular points of interest in Highland, or you can select a more remote option if you want a relaxing place to stay. Highland is known for its riverfront and mountain views.

What are some of the best vacation home rentals in Highland?

Our home is perfect for relaxing and having lots of fun, with near by activity’s: This highly rated vacation home rental in Highland offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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 will I find in Highland?

With 19 Expedia vacation rentals, you're sure to find just the right place for your Highland stay.

What can I see and do in Highland?

Walkway Over the Hudson State Historic Park and Berean Park Beach are a couple of scenic spots to enjoy the outdoors, whereas Franklin D Roosevelt Library & Museum is one of the cultural attractions. While here, Apple Greens Golf Course and Franny Reese State Park are other places worth a visit.

What are vacation rentals like in Highland?

Vacation rentals are privately owned properties you can book for a couple days or more in Highland. Vacation rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.