Highland Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Highland holiday rentals

Interior

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, (12 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 HK$1,763
HK$5,503 total
includes taxes & fees
3 Jun - 4 Jun
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

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, (1 review)
"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 HK$1,293
HK$3,011 total
includes taxes & fees
1 Jun - 2 Jun
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is HK$628
HK$1,047 total
includes taxes & fees
1 Jun - 2 Jun
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (4 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$973
HK$1,748 total
includes taxes & fees
31 May - 1 Jun
TRANQUIL MOUNTAIN SOLITUDE
Fridge, microwave, oven, stovetop

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.
The price is HK$603
HK$2,027 total
includes taxes & fees
3 Jun - 4 Jun
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (37 reviews)
"I was very happy with the property. I shared the place with my adult children for a family wedding. It was wonderful to have some quality, screenfree, engaging time with them. We took full advantage of the games and cards provided. The bedding was sooo comfy that I came home and ordered the same pillows that were there. I would definitely add the fact that the water is “well water” to the listing so people know in advance to bring water. All in all a great experience."
United States
Kim
The price is HK$492
HK$1,255 total
includes taxes & fees
3 Jun - 4 Jun
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Fireplace, books

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (14 reviews)
"The property was well maintained, it felt very cozy and well located in the town. Host were amazing as they were always present to help me with any problem I had even though I never needed them."
United States
Sebastian A.
The price is HK$558
HK$1,321 total
includes taxes & fees
3 Jun - 4 Jun
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Fridge, oven, stovetop, coffee/tea maker

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, (5 reviews)
The price is HK$797
HK$1,522 total
includes taxes & fees
4 Jun - 5 Jun
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is HK$670
HK$1,189 total
includes taxes & fees
1 Jun - 2 Jun
Glamping Tent & Campsite by Minnewaska State Park
Interior

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, (28 reviews)
"Clean and quiet."
United States
Ted
The price is HK$426
HK$1,190 total
includes taxes & fees
1 Jun - 2 Jun
Dream getaway apartment in the foot of Gunks Ridge
Interior

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (80 reviews)
"A quick stop over to explore Kingston and the surrounding area. We had a very nice time, thank you!"
United States
Lee M.
The price is HK$1,213
HK$1,946 total
includes taxes & fees
7 Jun - 8 Jun
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Interior

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is HK$721
HK$2,159 total
includes taxes & fees
2 Jun - 3 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
1 bedroom, free WiFi, bed sheets

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, (35 reviews)
"Instructions were clear. Accommodations were comfortable and clean. Lovely grounds. "
United States
Julia
The price is HK$882
HK$2,102 total
includes taxes & fees
31 May - 1 Jun
The Studio at the Inn at High Falls
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is HK$1,175
HK$2,296 total
includes taxes & fees
31 May - 1 Jun
Cozy country efficiency in the Hudson Valley
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is HK$901
HK$2,405 total
includes taxes & fees
3 Jun - 4 Jun
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio

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)
"Cozy, clean, and extremely accommodating. Everything was planned out well and the sauna was lovely in such cold weather! Would highly recommend for anyone considering travel to this beautiful region of New York!"
United States
Avi
The price is HK$361
HK$967 total
includes taxes & fees
3 Jun - 4 Jun
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Outdoor dining

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, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,011
HK$1,565 total
includes taxes & fees
31 May - 1 Jun
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$706
HK$816 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$980
HK$3,048 total
includes taxes & fees
2 Jun - 3 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!
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

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

6/10 Okay
"Rooms have funky odor. Staff was great and changed me to another one but still felt the odd smell. There was lot of smoking and weed doing on the property and inside the hallways. The AC also not adjustable inside the room. It’s auto on and off. During the night time it would get hot and suddenly cold. No pool. No breakfast. Gym is there but not even water and proper weights are present. This property looks like had its glory once upon a time. But currently in a bad condition. It has lot of potential but needs the necessary up keeping. Needs lot of improvements."
Usha 3-night trip
Posted 2 hours ago
The Crossroads Hotel, Newburgh

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!

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Frequently asked questions

Can I find holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its riverfront and mountain views.

What are some of the best holiday rentals that Highland has to offer?

The Farm at Hyde Park: This holiday home rental outside of Highland is located in a rural location, and has a fireplace, a patio and a BBQ 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 holiday rentals will I find in Highland?

With 18 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.