A suspension bridge over a river with autumn foliage and distant hills.

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Highland vacation rentals

A bedroom with a bed, a window, a heater, and a door leading to another room.

1. Hudson Valley Duplex: Hike, Sip + Explore!

Hudson Valley Duplex: Hike, Sip + Explore!
3.0 star property
Highland
Hudson Valley Duplex: Hike, Sip + Explore!
A porch with white railings and multiple chairs.

2. 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, (2 reviews)
"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.
$389 nightly
The price is $436
Oct 12 - Oct 13
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A spacious living area with a staircase, a dining table, and a sofa.

3. 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, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
$664 nightly
The price is $743
Oct 13 - Oct 14
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A wooden porch with white rocking chairs and a hanging flower basket.

4. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Would definitely stay again"
United States
Laurie G.
$355 nightly
The price is $398
Oct 12 - Oct 13
Total with taxes and fees
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

5. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (17 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$119 nightly
The price is $133
Nov 3 - Nov 4
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

6. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
$367 nightly
The price is $429
Oct 9 - Oct 10
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern kitchen with white cabinets, a central island, and a view to the outside.

7. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
$184 nightly
The price is $208
Oct 19 - Oct 20
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

8. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.8 out of 10, Excellent, (19 reviews)
"Clean cozy will be staying again"
United States
Michael C.
$161 nightly
The price is $164
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

9. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$71 nightly
The price is $80
Nov 2 - Nov 3
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

10. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (29 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
$198 nightly
The price is $234
Oct 14 - Oct 15
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

11. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
$221 nightly
The price is $248
Oct 14 - Oct 15
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A forest campsite with a tent, a fire pit, and a bench.

12. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
$136 nightly
The price is $152
Oct 12 - Oct 13
Total with taxes and fees
Glamping Tent & Campsite by Minnewaska State Park
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

13. 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, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
$243 nightly
The price is $287
Oct 18 - Oct 19
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
A brick building with a sign reading 'Lobby' in front.

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveler
$79 nightly
The price is $91
Nov 6 - Nov 7
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

15. 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, (46 reviews)
"The pictures are misleading"
United States
Jia
$240 nightly
The price is $268
Oct 11 - Oct 12
Total with taxes and fees
The Studio at the Inn at High Falls
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

16. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
$217 nightly
The price is $236
Oct 12 - Oct 13
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

17. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$237 nightly
The price is $265
Nov 3 - Nov 4
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A deck with a red umbrella, wooden chairs, and a table with potted plants.

18. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
$259 nightly
The price is $293
Nov 3 - Nov 4
Total with taxes and fees
Mid-Century DJ’s Dream
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

19. 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, (31 reviews)
"Wonderful property will definitely book again."
United States
Jane G.
$187 nightly
The price is $190
Nov 3 - Nov 4
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

20. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
$242 nightly
The price is $274
Oct 12 - Oct 13
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"Cleen room"
Giuseppe 2-night trip
Posted 4 hours ago
Beekman Arms and Delamater Inn

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 $91 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 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Highland?

With 30 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 lovely local spots to get outside and enjoy nature. 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.