A suspension bridge over a river with autumn foliage and distant hills.

Highland Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Highland holiday 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 HK$2,102
HK$4,444 total
includes taxes & fees
29 Jul - 30 Jul
Amazing 3-bedroom house with AC in adorable Highland
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 HK$1,568
HK$3,318 total
includes taxes & fees
16 Jul - 17 Jul
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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$2,342
HK$6,187 total
includes taxes & fees
22 Jul - 23 Jul
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
Jellystone Park Gardiner
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 HK$1,392
HK$2,204 total
includes taxes & fees
16 Jul - 17 Jul
Mid-Century DJ’s Dream
Property grounds

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (59 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is HK$1,524
HK$3,208 total
includes taxes & fees
20 Jul - 21 Jul
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Smart TV

The Loft At The Inn At High Falls

The Loft At The Inn At High Falls
High Falls
9.2 out of 10, Wonderful, (21 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
The price is HK$1,411
HK$2,774 total
includes taxes & fees
17 Jul - 18 Jul
The Loft At The Inn At High Falls
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, (90 reviews)
"Wonderful stay. "
United States
Chris L.
The price is HK$1,188
HK$1,857 total
includes taxes & fees
9 Aug - 10 Aug
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.8 out of 10, Exceptional, (11 reviews)
"Quiet and lovely for a solo adventure with my dog. "
United States
Darcie B.
The price is HK$1,254
HK$2,282 total
includes taxes & fees
16 Jul - 17 Jul
Tiny Home, King Bed & Hot Tub, Unit B
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$1,607
HK$2,886 total
includes taxes & fees
16 Jul - 17 Jul
Fabulous 3bdrm Home w/parking!
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
Charming Cabin in Fishkill!
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, (39 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is HK$1,162
HK$1,917 total
includes taxes & fees
28 Jul - 29 Jul
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
3.0 star property
Hyde Park
The price is HK$4,436
HK$7,730 total
includes taxes & fees
16 Jul - 17 Jul
Luxe Mountain Getaway on Private Rd Near Rhinebeck
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,325
HK$2,185 total
includes taxes & fees
19 Jul - 20 Jul
Cabin in the heart of the Hudson Valley, Cabin 3
Private kitchen

Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (5 reviews)
"The cabin is awesome. Surrounded by forrest you feel like youre the only person in the world. What's even cooler is its off grid but you dont miss a thing. Lights. Music. Bathroom. There were even a couple board games. Outside fire ready to go. Exactly what I was looking for."
United States
Carrie
The price is HK$894
HK$1,580 total
includes taxes & fees
16 Jul - 17 Jul
Woods Cabin-Kingston/Woodstock, NY.
Smart TV

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (28 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 HK$1,215
HK$2,493 total
includes taxes & fees
3 Aug - 4 Aug
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Interior

Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (16 reviews)
"The apartment was very clean and updated! Small back deck was nice to drink my morning coffee! Only issue was kids yelling and screaming in the neighborhood till almost 11pm."
United States
Donna
The price is HK$1,176
HK$2,081 total
includes taxes & fees
19 Jul - 20 Jul
Stunning and Cozy loft apartment in kingston .
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (35 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is HK$1,325
HK$2,213 total
includes taxes & fees
26 Jul - 27 Jul
Cabin in the Heart of the Hudson Valley, Cabin 1
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is HK$1,141
HK$2,105 total
includes taxes & fees
16 Jul - 17 Jul
Walk to WP Gate + Free Parking!
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 HK$670
HK$1,434 total
includes taxes & fees
21 Jul - 22 Jul
Dream getaway apartment in the foot of Gunks Ridge
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"The bed was the most comfortable of all my stays at different motels/hotels!! An easy on and off the highway. Delightful stay."
Mary J. 1-night trip
Posted 1 hour ago
Quality Inn & Suites Fishkill South near I-84

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 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 Studio at the Inn at High Falls: This holiday home rental outside of Highland 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 holiday rentals will I find in Highland?

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