Highland Vacation Rentals

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Our top choices for Highland vacation rentals

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.
$339 nightly
The price is $380
Jan 25 - Jan 26
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location and stay"
United States
kareem e.
$288 nightly
The price is $323
Jan 25 - Jan 26
Total with taxes and fees
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$231 nightly
The price is $259
Feb 14 - Feb 15
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (7 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$201 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$305 nightly
The price is $319
Jan 26 - Jan 27
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$438 nightly
The price is $445
Feb 10 - Feb 11
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
$216 nightly
The price is $249
Feb 10 - Feb 11
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
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.
$364 nightly
The price is $368
Jan 27 - Jan 28
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
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.
$159 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge

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.
$174 nightly
The price is $197
Jan 25 - Jan 26
Total with taxes and fees
Mid-Century DJ’s Dream
2.0 star property
$205 nightly
The price is $232
Jan 25 - Jan 26
Total with taxes and fees
Studio Lakeside Retreat Fast Wifi Great WFH
9.6 out of 10, Exceptional, (27 reviews)
"Very clean very comfortable beds."
United States
Millgate F.
$224 nightly
The price is $251
Feb 2 - Feb 3
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

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.
$206 nightly
The price is $233
Jan 26 - Jan 27
Total with taxes and fees
Private Studio Close to Downtown Rhinebeck
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.
$159 nightly
The price is $162
Jan 26 - Jan 27
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$510 nightly
The price is $576
Jan 26 - Jan 27
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms

Vacation Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very Good, (34 reviews)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
$240 nightly
The price is $268
Jan 25 - Jan 26
Total with taxes and fees
The Studio at the Inn at High Falls
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
$192 nightly
The price is $208
Jan 25 - Jan 26
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
9.4 out of 10, Exceptional, (22 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
$206 nightly
The price is $231
Jan 27 - Jan 28
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
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.
$308 nightly
The price is $348
Feb 4 - Feb 5
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
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

Find out more about Highland

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $226 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.