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

2. 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.
The price is ￥26,889
￥62,357 total
includes taxes & fees
Oct 26 - Oct 27
Step into history & unwind at Elixir 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
The price is ￥35,264
￥110,062 total
includes taxes & fees
Oct 27 - Oct 28
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A porch with white railings and multiple chairs.

4. 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.
The price is ￥31,634
￥68,026 total
includes taxes & fees
Oct 25 - Oct 26
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

5. 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.
The price is ￥25,179
￥67,306 total
includes taxes & fees
Oct 25 - Oct 26
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.

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, (12 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
The price is ￥17,632
￥32,535 total
includes taxes & fees
Nov 2 - Nov 3
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A deck with a red umbrella, wooden chairs, and a table with potted plants.

7. 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.
The price is ￥30,052
￥48,132 total
includes taxes & fees
Nov 2 - Nov 3
Mid-Century DJ’s Dream
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

8. 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.
The price is ￥27,250
￥35,469 total
includes taxes & fees
Oct 25 - Oct 26
Hudson Valley Farm Getaway- West/Llama Lover Lane
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.
The price is ￥39,543
￥65,369 total
includes taxes & fees
Nov 5 - Nov 6
Welcome to The Boathouse! Waterfront/Boats/Hot tub
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, (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
The price is ￥23,353
￥36,658 total
includes taxes & fees
Nov 1 - Nov 2
Cabin in the heart of the Hudson Valley, Cabin 4
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

11. 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.
The price is ￥26,487
￥45,174 total
includes taxes & fees
Nov 1 - Nov 2
Cabin in the Heart of the Hudson Valley, Cabin 1
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

12. 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.
The price is ￥18,980
￥44,376 total
includes taxes & fees
Nov 3 - Nov 4
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A cozy living room with a sofa, a dining table, and a bed.

13. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is ￥28,995
￥55,357 total
includes taxes & fees
Nov 1 - Nov 2
Cozy country efficiency in the Hudson Valley
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
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥12,401
￥14,339 total
includes taxes & fees
Nov 4 - Nov 5
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.

15. 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.
The price is ￥26,487
￥45,174 total
includes taxes & fees
Nov 5 - Nov 6
Cabin in the heart of the Hudson Valley, Cabin 3
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

16. 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
The price is ￥11,388
￥22,498 total
includes taxes & fees
Oct 28 - Oct 29
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A covered porch with a wooden deck, white columns, wicker chairs, and a view of a house with windows.

17. 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.
The price is ￥13,359
￥25,601 total
includes taxes & fees
Nov 1 - Nov 2
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

18. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (43 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.
The price is ￥23,510
￥69,864 total
includes taxes & fees
Oct 27 - Oct 28
The DeVita House Est. 1900
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

19. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is ￥23,353
￥36,843 total
includes taxes & fees
Nov 2 - Nov 3
Cabin in the heart of the Hudson Valley, Cabin 2
A living room with a fireplace, a painting, shelves with decorative items, and a television.

20. 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.
The price is ￥21,353
￥45,449 total
includes taxes & fees
Nov 9 - Nov 10
Grant - A Tranquil One Bedroom Steps from River
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

Kingston Regency Inn

Kingston Regency Inn

10/10 Excellent
"Everything was clean, everything worked as it should."
Christopher 1-night trip
Posted 2 hours ago
Kingston Regency Inn

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

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.