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.
$288 nightly
The price is $323
Feb 18 - Feb 19
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.
$339 nightly
The price is $380
Feb 18 - Feb 19
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Romantic Apartment in Historic Stone Ridge

Romantic Apartment in Historic Stone Ridge
Stone Ridge
9.4 out of 10, Exceptional, (21 reviews)
"Great stay!"
United States
Olivia O.
$158 nightly
The price is $160
Feb 18 - Feb 19
Total with taxes and fees
Romantic Apartment in Historic Stone 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.
$240 nightly
The price is $268
Feb 18 - Feb 19
Total with taxes and fees
The Studio at the Inn at High Falls

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
Feb 18 - Feb 19
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4

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.
$164 nightly
The price is $167
Feb 23 - Feb 24
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

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.
$317 nightly
The price is $332
Feb 18 - Feb 19
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Peaceful Lakeside Studio Fast Wifi Great WFH

Peaceful Lakeside Studio Fast Wifi Great WFH
2.0 star property
Monroe
$308 nightly
The price is $349
Feb 18 - Feb 19
Total with taxes and fees
Peaceful Lakeside Studio Fast Wifi Great WFH

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.
$236 nightly
The price is $279
Feb 18 - Feb 19
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

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.
$274 nightly
The price is $277
Feb 24 - Feb 25
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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.
$179 nightly
The price is $182
Feb 24 - Feb 25
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

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.
$413 nightly
The price is $419
Feb 18 - Feb 19
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (60 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
$280 nightly
The price is $280
Feb 18 - Feb 19
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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.
$233 nightly
The price is $261
Feb 23 - Feb 24
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!

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.
$159 nightly
The price is $162
Mar 3 - Mar 4
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge

West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (21 reviews)
"Very clean accommodations! Easy process from start to finish"
United States
Samantha R.
$176 nightly
The price is $197
Feb 18 - Feb 19
Total with taxes and fees
West Wing - a unique private space w/patio

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
$255 nightly
The price is $299
Feb 18 - Feb 19
Total with taxes and fees
King Bed | Private Parking | Strong WiFi

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (69 reviews)
"We came for our daughter’s wedding in town . The place was conveniently located near the wedding siteIt was small and just perfect for 3 members of my family -Woke up to birds chirping Would surely plan for a second stay "
United States
Pratistha L.
$202 nightly
The price is $226
Feb 22 - Feb 23
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!

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 location !"
United States
greg h.
$275 nightly
The price is $307
Feb 24 - Feb 25
Total with taxes and fees
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Retreat with Sauna in Historic Stone Ridge

Retreat with Sauna in Historic Stone Ridge
Stone Ridge
$220 nightly
The price is $223
Feb 18 - Feb 19
Total with taxes and fees
Retreat with Sauna in Historic Stone Ridge
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: Visitors like this Highland vacation home rental. It 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. Our travelers also rate Private 37 Acre Lake Estate on 164 Acres - 11 BR as a favorite home for rent in Highland.

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, 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.