Highland Vacation Rentals

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Our top choices for Highland vacation rentals

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.
$291 nightly
The price is $326
Feb 10 - Feb 11
Total with taxes and fees
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

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.
$382 nightly
The price is $428
Feb 10 - Feb 11
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

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, (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
Feb 10 - Feb 11
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
$210 nightly
The price is $242
Feb 10 - Feb 11
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
$299 nightly
The price is $312
Feb 10 - Feb 11
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
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.
$182 nightly
The price is $184
Feb 11 - Feb 12
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
Stone Ridge
9.0 out of 10, Wonderful, (15 reviews)
"Clean cozy will be staying again"
United States
Michael C.
$149 nightly
The price is $152
Feb 18 - Feb 19
Total with taxes and fees
Cozy Apartment with Sauna in Historic Stone Ridge

Studio Lakeside Retreat Fast Wifi Great WFH

Studio Lakeside Retreat Fast Wifi Great WFH
2.0 star property
Monroe
$190 nightly
The price is $214
Feb 10 - Feb 11
Total with taxes and fees
Studio Lakeside Retreat Fast Wifi Great WFH

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$223 nightly
The price is $250
Feb 25 - Feb 26
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (28 reviews)
"Very clean very comfortable beds."
United States
Millgate F.
$202 nightly
The price is $226
Feb 10 - Feb 11
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck
Rhinebeck Village
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
$209 nightly
The price is $236
Feb 10 - Feb 11
Total with taxes and fees
Private Studio Close to Downtown Rhinebeck

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, (16 reviews)
"Great Unit."
United States
Rudy R.
$294 nightly
The price is $299
Feb 17 - Feb 18
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
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.
$401 nightly
The price is $407
Feb 10 - Feb 11
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
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.
$387 nightly
The price is $393
Feb 10 - Feb 11
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.4 out of 10, Exceptional, (23 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
$197 nightly
The price is $221
Feb 10 - Feb 11
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
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.
$162 nightly
The price is $164
Feb 19 - Feb 20
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge

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)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
$243 nightly
The price is $272
Feb 10 - Feb 11
Total with taxes and fees
The Studio at the Inn at High Falls

Boutique King Suite at Orchard Lake Private Farm

Boutique King Suite at Orchard Lake Private Farm
2.0 star property
Monroe
$232 nightly
The price is $262
Feb 10 - Feb 11
Total with taxes and fees
Boutique King Suite at Orchard Lake Private Farm

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Woodstock
8.2 out of 10, Very Good, (10 reviews)
"Great place. Great location "
United States
Anonymous traveler
$289 nightly
The price is $324
Mar 3 - Mar 4
Total with taxes and fees
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
$169 nightly
The price is $200
Feb 10 - Feb 11
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
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 18 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.