Highland Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Highland vacation 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, (11 reviews)
"The house was great and the host was amazing!! We had a great time."
United States
Emma S.
The price is ￥35,694
￥111,759 total
includes taxes & fees
Apr 22 - Apr 23
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 ￥23,796
￥57,212 total
includes taxes & fees
Apr 22 - Apr 23
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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 ￥19,576
￥34,372 total
includes taxes & fees
May 19 - May 20
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, (5 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 ￥10,470
￥37,490 total
includes taxes & fees
Apr 22 - Apr 23
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, (34 reviews)
"Awesome place, great location. We loved our stay."
United States
Will R.
The price is ￥8,904
￥24,368 total
includes taxes & fees
Apr 27 - Apr 28
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

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, (22 reviews)
"Great stay!"
United States
Olivia O.
The price is ￥6,910
￥19,199 total
includes taxes & fees
Apr 26 - Apr 27
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
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, (25 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is ￥8,637
￥24,101 total
includes taxes & fees
Apr 23 - Apr 24
Dream getaway apartment in the foot of Gunks Ridge
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 ￥13,564
￥24,075 total
includes taxes & fees
Apr 22 - Apr 23
Glamping Tent & Campsite by Minnewaska State Park
2 bedrooms, desk, free WiFi, bed sheets

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is ￥13,019
￥45,522 total
includes taxes & fees
Apr 29 - Apr 30
Retro Retreat: renovated 2BR, desk, no chore list!
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is ￥16,118
￥33,143 total
includes taxes & fees
Apr 23 - Apr 24
Historic Cabin with Pool & Fire Pit
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is ￥9,966
￥23,842 total
includes taxes & fees
Apr 27 - Apr 28
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Private kitchen

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
10.0 out of 10, Exceptional, (1 review)
"This apartment was perfect! It was spotless and tastefully decorated. Fully supplied with everything you could possibly need. Very spacious and very cozy. The mattress was soooo comfortable and that’s real important to me. Coupons for the deli with the best sandwiches ever! The host was very nice and accommodated us for an earlier check in. I highly recommend this property!"
United States
Cathy T.
The price is ￥14,991
￥29,522 total
includes taxes & fees
Apr 28 - Apr 29
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
1 bedroom, WiFi, bed sheets

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Woodstock
8.2 out of 10, Very Good, (10 reviews)
"Great location !"
United States
greg h.
The price is ￥13,826
￥43,935 total
includes taxes & fees
Apr 28 - Apr 29
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Property grounds

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
9.0 out of 10, Wonderful, (15 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 ￥8,114
￥20,393 total
includes taxes & fees
Apr 29 - Apr 30
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Smart TV

King Bed | Private Parking | Strong WiFi

King Bed | Private Parking | Strong WiFi
Poughkeepsie
The price is ￥11,168
￥50,244 total
includes taxes & fees
Apr 22 - Apr 23
King Bed | Private Parking | Strong WiFi
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)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is ￥12,540
￥27,992 total
includes taxes & fees
May 6 - May 7
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
House | 7 bedrooms

Ready for Summer West Point - Jacuzzi Pool Games

Ready for Summer West Point - Jacuzzi Pool Games
2.0 star property
Cornwall
The price is ￥96,515
￥206,567 total
includes taxes & fees
Apr 27 - Apr 28
Ready for Summer West Point - Jacuzzi Pool Games
Exterior detail

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is ￥19,441
￥38,652 total
includes taxes & fees
Apr 22 - Apr 23
Cozy private suite in the heart of beautiful Gardiner.
Terrace/patio

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (28 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is ￥17,147
￥41,966 total
includes taxes & fees
Apr 27 - Apr 28
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (42 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is ￥21,434
￥46,699 total
includes taxes & fees
May 4 - May 5
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

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

10/10 Excellent
"Comfortable, spacious, clean, good breakfast spread, lots of housekeeping staff, pool & fitness facility were well maintained, everything stocked. Staff was kind , attentive but not intrusive. I will definitely be staying here again"
Theresa 3-night trip
Posted 8 hours ago
Home2 Suites By Hilton Poughkeepsie

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 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 14 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 19 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.