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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Highland vacation rentals

Paper towels

Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is ￥39,226
￥86,693 total
includes taxes & fees
Jul 27 - Jul 28
Amazing 3-bedroom house with AC in adorable Highland
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 ￥47,631
￥128,955 total
includes taxes & fees
Jul 28 - Jul 29
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, (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 ￥32,620
￥69,415 total
includes taxes & fees
Aug 6 - Aug 7
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Exterior

Spacious Peaceful 5 BR Home with a View in Hudson Valley

Spacious Peaceful 5 BR Home with a View in Hudson Valley
Highland
The price is ￥358,820
￥518,058 total
includes taxes & fees
Aug 6 - Aug 7
Spacious Peaceful 5 BR Home with a View in Hudson 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, (8 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 ￥13,064
￥21,791 total
includes taxes & fees
Aug 4 - Aug 5
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Smart TV

The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (35 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is ￥24,465
￥72,521 total
includes taxes & fees
Aug 6 - Aug 7
The DeVita House Est. 1900
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (11 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 ￥24,037
￥41,236 total
includes taxes & fees
Jul 30 - Jul 31
TRANQUIL MOUNTAIN SOLITUDE
Property grounds

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Newburgh
10.0 out of 10, Exceptional, (72 reviews)
"Great place for a few days R & R. Definately recommended"
United States
Mary R.
The price is ￥14,599
￥35,634 total
includes taxes & fees
Jul 27 - Jul 28
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥11,207
￥23,889 total
includes taxes & fees
Jul 29 - Jul 30
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Coffee/tea maker, fridge, oven, stovetop

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)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is ￥18,728
￥34,348 total
includes taxes & fees
Aug 5 - Aug 6
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (54 reviews)
"Kevin's place is lovely. Would definitely stay again when visiting the area. Great location for our needs. "
United States
Sue T.
The price is ￥22,312
￥37,232 total
includes taxes & fees
Jul 29 - Jul 30
Mid-Century DJ’s Dream
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)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is ￥21,137
￥32,905 total
includes taxes & fees
Jul 27 - Jul 28
Cabin in the heart of the Hudson Valley, Cabin 4
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, (40 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is ￥13,868
￥28,188 total
includes taxes & fees
Jul 28 - Jul 29
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Property grounds

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, (88 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is ￥16,359
￥35,127 total
includes taxes & fees
Jul 26 - Jul 27
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

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 ￥47,910
￥100,063 total
includes taxes & fees
Jul 27 - Jul 28
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
1 bedroom, WiFi (free), 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, (40 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 ￥18,349
￥43,750 total
includes taxes & fees
Jul 26 - Jul 27
The Studio at the Inn at High Falls
Property grounds

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 ￥13,945
￥24,752 total
includes taxes & fees
Aug 6 - Aug 7
Glamping Tent & Campsite by Minnewaska State Park
Coffee/tea maker, fridge, microwave, oven

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 ￥13,600
￥43,676 total
includes taxes & fees
Jul 27 - Jul 28
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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, (29 reviews)
"The kitchen was great, lots of tools, fun to cook in! "
United States
Brooke H.M. S.
The price is ￥19,213
￥35,647 total
includes taxes & fees
Aug 6 - Aug 7
Dream getaway apartment in the foot of Gunks Ridge
Lobby

1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveler
The price is ￥17,977
￥20,336 total
includes taxes & fees
Aug 15 - Aug 16
1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"Safe, comfortable, easy access to highway. Staff were helpful in choosing room for wheelchair accessibility. A/C in room 133 needs attention, fan is extremely noisy."
MILDRED 1-night trip
Posted less than an hour ago
Holiday Inn Express Poughkeepsie by IHG

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!

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 Studio at the Inn at High Falls: Visitors like this Highland vacation home rental. It is located in a rural location and offers a garden, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals will I find in Highland?

With 21 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, Apple Greens Golf Course and Franny Reese State Park 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.