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

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.
$287 nightly
The price is $321
Apr 1 - Apr 2
Total with taxes and fees
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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.
$628 nightly
The price is $703
Apr 3 - Apr 4
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
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.
$376 nightly
The price is $421
Apr 1 - Apr 2
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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.
$237 nightly
The price is $280
Apr 1 - Apr 2
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
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
$271 nightly
The price is $304
Apr 1 - Apr 2
Total with taxes and fees
Tiny Home, King Bed & Hot Tub, Unit B
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.
$182 nightly
The price is $205
Apr 9 - Apr 10
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
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
Apr 2 - Apr 3
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
Outdoor dining

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, (62 reviews)
"For us it was in a great location, had a reasonable price and room for everyone."
United States
Gertrude (Gert) P.
$276 nightly
The price is $319
Apr 2 - Apr 3
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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.
$165 nightly
The price is $168
Apr 1 - Apr 2
Total with taxes and fees
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (73 reviews)
"Clean and comfortable! Pet friendly! Quick scenic ride into Kingston downtown. Not a true 3 bedroom with privacy but more a 2 bedroom (one is in the loft) plus pull out couch. This worked out well for our long weekend getaway."
United States
Debra
$212 nightly
The price is $237
Apr 5 - Apr 6
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Property grounds

Fall Foliage Getaway!

Fall Foliage Getaway!
Woodstock
10.0 out of 10, Exceptional, (12 reviews)
"We loved the place - beautiful house and setting."
United States
Michele P.
$655 nightly
The price is $734
Apr 1 - Apr 2
Total with taxes and fees
Fall Foliage Getaway!
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
$382 nightly
The price is $435
Apr 1 - Apr 2
Total with taxes and fees
Rustic Cabin in Fishkill!
2 bedrooms, desk, iron/ironing board, travel crib

Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston

Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Kingston
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time. Place is convenient located in proximity of Rosendale and Kingston "
United States
Carol N.
$338 nightly
The price is $378
Apr 1 - Apr 2
Total with taxes and fees
Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
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.
$431 nightly
The price is $488
Apr 1 - Apr 2
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior

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.
$149 nightly
The price is $152
Apr 1 - Apr 2
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Private kitchen

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
9.4 out of 10, Exceptional, (6 reviews)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
$686 nightly
The price is $768
Apr 12 - Apr 13
Total with taxes and fees
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Fridge, microwave, oven, stovetop

New Farmhouse-Hot Tub, King Beds, Game Room & View

New Farmhouse-Hot Tub, King Beds, Game Room & View
Montgomery
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."
United States
Emily B.
$1,036 nightly
The price is $1,183
Apr 1 - Apr 2
Total with taxes and fees
New Farmhouse-Hot Tub, King Beds, Game Room & View
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.
$365 nightly
The price is $387
Apr 1 - Apr 2
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (78 reviews)
"great location and nice host"
United States
christopher s.
$236 nightly
The price is $264
Apr 1 - Apr 2
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
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 1 - Apr 2
Total with taxes and fees
Cozy private suite in the heart of beautiful Gardiner.
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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent
"Hotel gym was fantastic, storyteller restaurant food & drinks amazing. One of the best complimentary breakfasts we’ve ever had. Plan on returning. 5 stars all the way!"
Laura 1-night trip
Posted 5 hours ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

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 $237 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?

Private 37 Acre Lake Estate on 164 Acres - 11 BR: This highly rated vacation home rental in Highland is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 14 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

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.