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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Highland vacation rentals

A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

1. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is AED 1,008
AED 1,931 total
includes taxes & fees
5 Oct - 6 Oct
Amazing 3-bedroom house with AC in adorable Highland
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)
"Great apt for my mom who has limited mobility. Totally accessible and very comfortable. "
United States
Ellen E.
The price is AED 624
AED 1,341 total
includes taxes & fees
30 Sep - 1 Oct
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A porch with white railings and multiple chairs.

3. 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 AED 624
AED 1,337 total
includes taxes & fees
5 Oct - 6 Oct
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.

4. 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 AED 1,014
AED 2,633 total
includes taxes & fees
27 Oct - 28 Oct
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Interior

5. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View
Highland
The price is AED 1,901
AED 3,347 total
includes taxes & fees
1 Oct - 2 Oct
Hudson Escape W/ Hot Tub + Bridge View
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.
The price is AED 590
AED 1,496 total
includes taxes & fees
30 Sep - 1 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

7. 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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AED 257
AED 514 total
includes taxes & fees
20 Oct - 21 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A deck with a red umbrella, wooden chairs, and a table with potted plants.

8. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (59 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AED 585
AED 911 total
includes taxes & fees
4 Oct - 5 Oct
Mid-Century DJ’s Dream
A modern kitchen with white cabinets, a central island, and a view to the outside.

9. 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, (9 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AED 423
AED 770 total
includes taxes & fees
30 Sep - 1 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
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.

10. 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
The price is AED 413
AED 993 total
includes taxes & fees
30 Sep - 1 Oct
The Studio at the Inn at High Falls
A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

11. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
The price is AED 788
AED 2,446 total
includes taxes & fees
4 Oct - 5 Oct
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

12. 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, (101 reviews)
"We were very happy with the house and location, but what made it amazing was how great host was. Very accommodating and helpful with helping us out last minute. Would absolutely recommend working with this host again."
United States
Chris W.
The price is AED 506
AED 990 total
includes taxes & fees
8 Oct - 9 Oct
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

13. 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, (40 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 AED 547
AED 820 total
includes taxes & fees
30 Sep - 1 Oct
Cabin in the heart of the Hudson Valley, Cabin 2
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

14. 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.
The price is AED 633
AED 807 total
includes taxes & fees
30 Sep - 1 Oct
Hudson Valley Farm Getaway- West/Llama Lover Lane
A wooden vanity with a mirror, two pendant lights, and a folded towel.

15. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Stone Ridge
9.4 out of 10, Exceptional, (30 reviews)
"Great location close to town. Cute and clean. Great little spot."
United States
Stephen
The price is AED 195
AED 479 total
includes taxes & fees
30 Sep - 1 Oct
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

16. 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 AED 621
AED 994 total
includes taxes & fees
30 Sep - 1 Oct
Cabin in the Heart of the Hudson Valley, Cabin 1
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

17. 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.
The price is AED 286
AED 644 total
includes taxes & fees
30 Sep - 1 Oct
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.

18. 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.
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A modern living room with a large window, a fireplace, and a cozy seating area.

19. Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (24 reviews)
"My husband and I had a lovely stay at the Mossy Moody Cabin. Mackenzie was a great host, easy to communicate with, and the cabin had everything we needed. The hot tub was such a nice feature too. It was close to town but nice and private- we loved it!"
United States
Jennifer M.
The price is AED 770
AED 1,640 total
includes taxes & fees
5 Oct - 6 Oct
Mossy Moody Cabin in High Falls, NY
A rustic cabin with a wooden barrel entrance, stone fire pit, and outdoor seating area surrounded by a forest.

20. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
9.8 out of 10, Exceptional, (27 reviews)
"Perfect for a short get away"
United States
Darryl
The price is AED 546
AED 904 total
includes taxes & fees
30 Sep - 1 Oct
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"Nice hotel. Good quality. Spotless clean"
Lei 1-night trip
Posted 1 hour ago
Quality Inn Hyde Park Poughkeepsie North

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.