Highland Vacation Rentals from $224: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Highland vacation rentals

Apartment in Highland

kareem e.

$288 nightly

Mar 9 - Mar 10

Total with taxes and fees

Apartment in Highland

Rebecca D.

$350 nightly

Mar 9 - Mar 10

Total with taxes and fees

Vacation Home in Kerhonkson

Julia K.

$159 nightly

Mar 10 - Mar 11

Total with taxes and fees

Cottage in Kerhonkson

Patrick S.

$178 nightly

Mar 11 - Mar 12

Total with taxes and fees

Vacation Home in High Falls

dianna i.

$240 nightly

Mar 9 - Mar 10

Total with taxes and fees

Cabin in Newburgh

jennifer w.

$169 nightly

Mar 9 - Mar 10

Total with taxes and fees

Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Rudy R.

$256 nightly

Mar 9 - Mar 10

Total with taxes and fees

Apartment in Kingston

Millgate F.

$200 nightly

Mar 9 - Mar 10

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Highland Hotel Reviews

Hampton Inn by Hilton New Paltz

10/10 Excellent

"Everything was great. Excellent location right off NY State Thruway and only about a mile from downtown shops. Sideshow Kitchen and Bar, about a mile away, has the best steak sandwich I ever had. Be sure to check out the Tibetan shop in town too. I’ll be back!"

Residence Inn by Marriott Kingston

8/10 Good

"The young Lady that was working the front desk on the morning of Monday and Tuesday March 2nd and 3rd, needs some training in customer service. I asked her a simple question about switching out the towels in my room because I was there for a few days, she was very rude and disrespectful. The next day as I was in the breakfast area I could see her on the phone at the front desk and when she hung up the phone she was flailing her arms in the air as if she were having a temper tantrum. "

Woodstock Way Hotel

8/10 Good

"Rooms were very clean. After hour support was great when we had an issue with the heat not working in our original premium room (big issue when it’s 20 degrees out). Thankfully they were practically empty and were able to switch to a comparable room in the next building. Addie was by far our favorite staff member who was full of life and cheer. Espresso on tap was a plus just wish it was in the room itself. WiFi was TERRIBLE. If you expect to get any work done while away which is very important or would like to stream a show in the cabins, think again lol. The beds & couches were super comfy. The worst part of the room besides the WiFi was the TV. It was beyond mediocre for the sheer size of the room. You could not comfortably see it from the bed or the couch. Also because of the terrible WiFi the tv would constantly cut out. Other wise the local area restaurants are great. Other than that there is not much to do if you do not ski. 2 nights is more than enough. Maybe the summer is better"

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 $224 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?

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 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.

Highland Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Highland vacation rentals

Apartment in Highland

Apartment in Highland

Vacation Home in Kerhonkson

Cottage in Kerhonkson

Vacation Home in High Falls

Cabin in Newburgh

Apartment in Highland Falls

Apartment in Kingston

Vacation Home in Kingston

Apartment in Kingston

Apartment in Wallkill

Cabin in Montgomery

Cabin in Newburgh

Apartment in Stone Ridge

Vacation Home in Kingston

Apartment in Rhinebeck Village

Vacation Home in Highland Falls

Apartment in Kingston

Vacation Home in Fishkill

Apartment in Shokan

The Annual Vacation Sale

Find vacation rentals that suit your style

Top Highland Hotel Reviews

Hampton Inn by Hilton New Paltz

Find out more about Highland

Explore a world of travel with Expedia

Trending destinations on Expedia.com

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app