Highland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Highland vacation rentals

Terrace/patio

Apartment in Highland

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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.
$350 nightly
The price is $392
Mar 4 - Mar 5
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Interior

Vacation Home in Kingston

Esopus Creek modern Tiny house Retreat!
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.
$199 nightly
The price is $223
Mar 4 - Mar 5
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Terrace/patio

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$236 nightly
The price is $279
Mar 4 - Mar 5
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Outdoor dining

Vacation Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.4 out of 10, Exceptional, (61 reviews)
"Best place ever, various entertainment options from projector to tvs. "
United States
Mahbub Ridhoo M.
$276 nightly
The price is $319
Mar 4 - Mar 5
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in Newburgh

Cabin in the Heart of the Hudson Valley, Cabin 1
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
Mar 4 - Mar 5
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
Exterior

Apartment in Millbrook

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
$433 nightly
The price is $490
Mar 4 - Mar 5
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Property grounds

Vacation Home in Woodstock

Fall Foliage Getaway!
10.0 out of 10, Exceptional, (12 reviews)
"We loved the place - beautiful house and setting."
United States
Michele P.
$642 nightly
The price is $719
Mar 4 - Mar 5
Total with taxes and fees
Fall Foliage Getaway!
Fridge, microwave, oven, stovetop

Vacation Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$529 nightly
The price is $599
Mar 9 - Mar 10
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior

Cabin in Fishkill

Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
$402 nightly
The price is $458
Mar 9 - Mar 10
Total with taxes and fees
Rustic Cabin in Fishkill!
Property grounds

Vacation Home in wallkill

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
9.8 out of 10, Exceptional, (57 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
$317 nightly
The price is $355
Mar 4 - Mar 5
Total with taxes and fees
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Newburgh

Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (67 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
$265 nightly
The price is $313
Mar 4 - Mar 5
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Interior

Vacation Home in Lake Katrine

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"Perfect getaway!"
United States
Lynn A.
$371 nightly
The price is $416
Mar 4 - Mar 5
Total with taxes and fees
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Interior

Vacation Home in West Hurley

Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience
10.0 out of 10, Exceptional, (5 reviews)
"very relaxing and comfortable place to stay!"
United States
Tilson
$771 nightly
The price is $864
Mar 4 - Mar 5
Total with taxes and fees
Nature Mountain Retreat with Outdoor Hot Tub and Sauna Spa Experience
Property grounds

Vacation Home in Cornwall

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
10.0 out of 10, Exceptional, (6 reviews)
$339 nightly
The price is $400
Mar 4 - Mar 5
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
TV

Apartment in Highland Falls

Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (21 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
$217 nightly
The price is $238
Mar 4 - Mar 5
Total with taxes and fees
Walk to WP Gate + Free Parking!
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Zero complaints. Excellent stay all around!"
Chriselle 2-night trip
Posted 15 hours ago
Hampton Inn by Hilton New Paltz

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 $223 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, 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.