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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Highland vacation rentals

Paper towels

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

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is AED 770
AED 1,809 total
includes taxes & fees
17 Aug - 18 Aug
Amazing 3-bedroom house with AC in adorable Highland
Terrace/patio

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.
The price is AED 735
AED 1,567 total
includes taxes & fees
17 Aug - 18 Aug
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Interior

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 AED 1,021
AED 2,830 total
includes taxes & fees
8 Sep - 9 Sep
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Property grounds

4. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (57 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AED 488
AED 822 total
includes taxes & fees
17 Aug - 18 Aug
Mid-Century DJ’s Dream
Smart TV, fireplace

5. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is AED 555
AED 840 total
includes taxes & fees
17 Aug - 18 Aug
Private, Cozy, Clean apartment in lovely Hyde Park
Coffee/tea maker, fridge, oven, stovetop

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (6 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AED 415
AED 773 total
includes taxes & fees
14 Sep - 15 Sep
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Exterior

7. 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, (38 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 474
AED 742 total
includes taxes & fees
16 Aug - 17 Aug
Cabin in the heart of the Hudson Valley, Cabin 2
Interior

8. 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, (4 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 1,135
AED 2,332 total
includes taxes & fees
14 Sep - 15 Sep
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Property grounds

9. 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 832 total
includes taxes & fees
17 Aug - 18 Aug
Hudson Valley Farm Getaway- West/Llama Lover Lane
1 bedroom, WiFi (free), bed sheets

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, (41 reviews)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
United States
Jamie M.
The price is AED 413
AED 998 total
includes taxes & fees
16 Aug - 17 Aug
The Studio at the Inn at High Falls
Smart TV

11. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (37 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is AED 551
AED 1,645 total
includes taxes & fees
16 Aug - 17 Aug
The DeVita House Est. 1900
1 bedroom, iron/ironing board, WiFi (free), bed sheets

12. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (72 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is AED 679
AED 1,315 total
includes taxes & fees
17 Aug - 18 Aug
Cozy country efficiency in the Hudson Valley
Property grounds

13. 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, (92 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is AED 362
AED 792 total
includes taxes & fees
17 Aug - 18 Aug
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Terrace/patio

14. 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
8.6 out of 10, Excellent, (17 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is AED 327
AED 615 total
includes taxes & fees
18 Aug - 19 Aug
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Interior

15. 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, (30 reviews)
"The kitchen was great, lots of tools, fun to cook in! "
United States
Brooke H.M. S.
The price is AED 338
AED 696 total
includes taxes & fees
7 Sep - 8 Sep
Dream getaway apartment in the foot of Gunks Ridge
1 bedroom, WiFi (free)

16. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is AED 299
AED 338 total
includes taxes & fees
1 Sep - 2 Sep
2 Queen Beds | Non-Smoking, Kitchen
Terrace/patio

17. 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, (20 reviews)
"Clean, comfortable cabin near New Paltz. Great views, well stocked kitchen."
United States
Heather G.
The price is AED 874
AED 1,314 total
includes taxes & fees
9 Sep - 10 Sep
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Property grounds

18. 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.
The price is AED 314
AED 557 total
includes taxes & fees
16 Aug - 17 Aug
Glamping Tent & Campsite by Minnewaska State Park
1 bedroom, iron/ironing board, WiFi (free), bed sheets

19. 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 overnight spot, especially with a dog."
United States
Ed C.
The price is AED 621
AED 1,037 total
includes taxes & fees
16 Aug - 17 Aug
Cabin in the Heart of the Hudson Valley, Cabin 1
Smart TV

20. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (29 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
The price is AED 459
AED 1,020 total
includes taxes & fees
10 Sep - 11 Sep
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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
"Charming, and Historic!!"
Raymond 2-night trip
Posted 4 hours ago
Beekman Arms and Delamater Inn

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?

The Farm at Hyde Park: Visitors like this Highland vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Highland?

With 25 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.