Highland Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Highland vacation rentals

Interior

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (11 reviews)
"The house was great and the host was amazing!! We had a great time."
United States
Emma S.
$629 nightly
The price is $704
Apr 6 - Apr 7
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Property grounds

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Highland
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location and stay"
United States
kareem e.
$288 nightly
The price is $323
Apr 6 - Apr 7
Total with taxes and fees
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Terrace/patio

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
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.
$378 nightly
The price is $423
Apr 8 - Apr 9
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Outdoor dining

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$213 nightly
The price is $241
May 6 - May 7
Total with taxes and fees
Glamping, family fun, pet friendly
1 bedroom, free WiFi, bed sheets

The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very Good, (34 reviews)
"Instructions were clear. Accommodations were comfortable and clean. Lovely grounds. "
United States
Julia
$240 nightly
The price is $268
Apr 6 - Apr 7
Total with taxes and fees
The Studio at the Inn at High Falls
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
$169 nightly
The price is $200
Apr 6 - Apr 7
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$185 nightly
The price is $209
Apr 9 - Apr 10
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
Fridge, microwave, oven, stovetop

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
$210 nightly
The price is $235
Apr 7 - Apr 8
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (34 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$174 nightly
The price is $176
Apr 15 - Apr 16
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (18 reviews)
"Great Unit."
United States
Rudy R.
$299 nightly
The price is $303
Apr 6 - Apr 7
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Exterior detail

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
New Paltz
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.
$218 nightly
The price is $244
Apr 6 - Apr 7
Total with taxes and fees
Cozy private suite in the heart of beautiful Gardiner.
Interior

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
9.0 out of 10, Wonderful, (15 reviews)
"Cozy, clean, and extremely accommodating. Everything was planned out well and the sauna was lovely in such cold weather! Would highly recommend for anyone considering travel to this beautiful region of New York!"
United States
Avi
$122 nightly
The price is $124
May 6 - May 7
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Smart TV

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (25 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
$205 nightly
The price is $230
Apr 8 - Apr 9
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
$136 nightly
The price is $152
Apr 19 - Apr 20
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park
2 bedrooms, desk, free WiFi, bed sheets

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
$257 nightly
The price is $288
Apr 29 - Apr 30
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.6 out of 10, Exceptional, (9 reviews)
"Everything was perfect. Don’t miss the owners restaurant either it’s great "
United States
Matthew
$268 nightly
The price is $300
Apr 7 - Apr 8
Total with taxes and fees
Tiny Home, King Bed & Hot Tub, Unit B
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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
$369 nightly
The price is $391
Apr 6 - Apr 7
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Smart TV, fireplace

Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (18 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
$348 nightly
The price is $390
Apr 8 - Apr 9
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
$166 nightly
The price is $169
Apr 15 - Apr 16
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
$239 nightly
The price is $282
Apr 6 - Apr 7
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
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

Mirbeau Inn & Spa

Mirbeau Inn & Spa

10/10 Excellent
"We only stayed overnight as we were traveling through the area, but we did order dinner on room service which was delicious. The room was very pretty and clean and quiet. It’s right in town so you can walk around. "
Christina 1-night trip
Posted 5 hours ago
Mirbeau Inn & Spa

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 $234 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.

Explore a world of travel with Expedia

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?

Esopus Creek modern Tiny house Retreat!: Visitors like this Highland vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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, Franny Reese State Park and Apple Greens Golf Course 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.