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Highland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Highland vacation rentals

Terrace/patio
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Vacation Home in Highland

9.6 out of 10, Exceptional, (11)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Outdoor dining
The Scenic Mansion With Breathtaking View

Villa in Highland

8.8 out of 10, Excellent, (18)
"Great facilities: pool, tennis/pickleball court, big screen tv. Clean. Weather was great so we didn't use AC or heat. Very scenic views. "
United States
Jeremy B.
The Scenic Mansion With Breathtaking View
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Cottage in Woodstock

10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is ￥24,934
￥52,867 total
includes taxes & fees
Dec 13 - Dec 14
Streamside Cottage Half Mile to Town of Woodstock
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Vacation Home in Kingston

9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is ￥23,288
￥36,972 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Esopus Creek modern Tiny house Retreat!
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Vacation Home in Fishkill

9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
The price is ￥38,558
￥49,259 total
includes taxes & fees
Dec 11 - Dec 12
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior
The Farm at Hyde Park

Vacation Home in Staatsburg

9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Cottage in West Shokan

10.0 out of 10, Exceptional, (54)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Interior
Large,Cozy,Bright Apartment, Business Themed.

Vacation Home in Newburgh

9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥56,084
￥74,715 total
includes taxes & fees
Dec 11 - Dec 12
Large,Cozy,Bright Apartment, Business Themed.
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cottage in woodstock

9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is ￥28,042
￥48,158 total
includes taxes & fees
Dec 14 - Dec 15
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio
Hamptons on the Hudson in South Saugerties

Vacation Home in Glasco

10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
1 bedroom, desk, free WiFi
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Apartment in Red Hook

9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
The price is ￥19,630
￥34,014 total
includes taxes & fees
Dec 11 - Dec 12
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Exterior
TRANQUIL MOUNTAIN SOLITUDE

Mobile Home in Pine Bush

10.0 out of 10, Exceptional, (4)
"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 ￥19,336
￥34,653 total
includes taxes & fees
Dec 20 - Dec 21
TRANQUIL MOUNTAIN SOLITUDE
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Apartment in Kingston

9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is ￥13,320
￥36,380 total
includes taxes & fees
Dec 11 - Dec 12
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Outdoor dining
Mid-Century DJ’s Dream

Apartment in Staatsburg

10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is ￥17,410
￥30,623 total
includes taxes & fees
Dec 18 - Dec 19
Mid-Century DJ’s Dream
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Cabin in Saugerties

9.0 out of 10, Wonderful, (13)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
Property grounds
Wappinger Cottage - Scandinavian retreat on a creek

Cottage in Poughkeepsie

10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!

Vacation Home in New Paltz

10.0 out of 10, Exceptional, (136)
"Great location, comfortable cabin, responsive host!"
United States
Theresa M.
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Exterior
Rustic Cabin in Fishkill!

Cabin in Fishkill

10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥47,126
￥70,421 total
includes taxes & fees
Dec 11 - Dec 12
Rustic Cabin in Fishkill!
Children's area
Hickory on Willow Lake

Vacation Home in Fishkill

9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is ￥59,979
￥88,133 total
includes taxes & fees
Dec 29 - Dec 30
Hickory on Willow Lake
Exterior
Mountain View escape

Cottage in New Paltz

10.0 out of 10, Exceptional, (69)
"Really cute cottage with a view of Skytop and the mountains. Quiet location. Fully equipped kitchen. Enjoyed our stay very much. "
United States
barbara d.
Mountain View escape
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

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Buisness friendly, breakfast, gym room, quiet, good customer service "
Luna 1-night trip
Posted 1 day ago
Courtyard by Marriott 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
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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?

Our home is perfect for relaxing and having lots of fun, with near by activity’s: This highly rated vacation home rental in Highland offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. 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 18 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.