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

Highland Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Highland vacation rentals

A wooden porch with white rocking chairs and a hanging flower basket.

1. 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.
$352 nightly
The price is $394
Oct 26 - Oct 27
Total with taxes and fees
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
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.
$386 nightly
The price is $432
Oct 26 - Oct 27
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
$627 nightly
The price is $702
Oct 27 - Oct 28
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
$370 nightly
The price is $433
Oct 26 - Oct 27
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A room with a large bookshelf filled with books and DVDs, a bed, a small table with a lamp, and a window with blinds.

5. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
$225 nightly
The price is $254
Oct 26 - Oct 27
Total with taxes and fees
Mid-Century DJ’s Dream
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
$184 nightly
The price is $208
Nov 2 - Nov 3
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A compact kitchen with white cabinets, a black refrigerator, and a microwave. There is a wooden dining table with a chair, and a sofa with a decorative pillow.

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

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
$207 nightly
The price is $225
Oct 26 - Oct 27
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
A covered outdoor area with a barbecue grill and a hot tub.

8. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (42 reviews)
"Really nice, house. Location was great. There were 8 of us there for a girls weekend. Plenty of room for all.Clean, attentive host, kitchen was well stocked for our needs. Hot tub was great."
United States
Shirley A.
$342 nightly
The price is $347
Oct 29 - Oct 30
Total with taxes and fees
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A hot tub on a wooden deck with a view of a river and trees.

9. Welcome to The Boathouse! Waterfront/Boats/Hot tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
$369 nightly
The price is $413
Nov 5 - Nov 6
Total with taxes and fees
Welcome to The Boathouse! Waterfront/Boats/Hot tub
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

10. 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
$79 nightly
The price is $89
Oct 27 - Oct 28
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
$79 nightly
The price is $91
Nov 3 - Nov 4
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

12. 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, (20 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$244 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
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.
$244 nightly
The price is $288
Oct 26 - Oct 27
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

14. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (44 reviews)
"We really enjoyed a second stay at the De Vita House. The place is so clean and comfortable, and the location is great. Karin is a great host--she immediately dropped off a couple kitchen items we thought we needed--wasn't even an emergency or anything! Absolutely recommend."
United States
Natalie R.
$398 nightly
The price is $446
Oct 27 - Oct 28
Total with taxes and fees
The DeVita House Est. 1900
A cozy living room with a sofa, a dining table, and a bed.

15. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Lovely cottage in a beautiful setting with everything you need to rest, relax, and enjoy this lovely part of New York state. Highly recommend!"
United States
Frances N.
$299 nightly
The price is $353
Oct 26 - Oct 27
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
A living room with a fireplace, a painting, shelves with decorative items, and a television.

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$254 nightly
The price is $287
Nov 9 - Nov 10
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

17. 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.
$251 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

18. 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, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
$198 nightly
The price is $234
Oct 27 - Oct 28
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

19. 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.
$135 nightly
The price is $138
Nov 1 - Nov 2
Total with taxes and fees
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A two-story house with a front porch and a landscaped garden.

20. 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, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$127 nightly
The price is $142
Oct 28 - Oct 29
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

8/10 Good
"Comfortable bed. Helpful staff. Good location."
Patrick 1-night trip
Posted 13 hours ago
Holiday Inn Express Poughkeepsie by IHG

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.