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Highland Vacation Rentals

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Nov 29 - Nov 30
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Vacation Rentals in 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, (1)
"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 ￥31,236
￥66,295 total
includes taxes & fees
Nov 30 - Dec 1
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Exterior
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

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 ￥19,257
￥34,686 total
includes taxes & fees
Nov 30 - Dec 1
TRANQUIL MOUNTAIN SOLITUDE
Apartment, 2 Bedrooms, Balcony, Garden View | Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

2.0 star property
Poughkeepsie
10.0 out of 10, Exceptional, (5)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
The price is ￥36,274
￥42,485 total
includes taxes & fees
Nov 30 - Dec 1
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is ￥32,954
￥52,876 total
includes taxes & fees
Dec 15 - Dec 16
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Fridge, microwave, oven, stovetop
Higashi: New Paltz family home with King bed minutes to downtown

Higashi: New Paltz family home with King bed minutes to downtown

New Paltz
9.8 out of 10, Exceptional, (20)
"Great place to stay! We enjoyed our time here. "
United States
Christy B.
The price is ￥14,843
￥48,459 total
includes taxes & fees
Dec 18 - Dec 19
Higashi: New Paltz family home with King bed minutes to downtown
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is ￥17,192
￥37,966 total
includes taxes & fees
Dec 14 - Dec 15
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
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, (4)
"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 ￥21,709
￥52,127 total
includes taxes & fees
Dec 27 - Dec 28
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior
Modern Hudson Valley Retreat Near Mohonk

Modern Hudson Valley Retreat Near Mohonk

2.0 star property
Plattekill
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
The price is ￥15,321
￥41,122 total
includes taxes & fees
Dec 1 - Dec 2
Modern Hudson Valley Retreat Near Mohonk
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥9,996
￥37,609 total
includes taxes & fees
Dec 3 - Dec 4
Campfire Cottage: Fireplace, fire pit & no chores!
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, (7)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is ￥19,960
￥40,371 total
includes taxes & fees
Dec 1 - Dec 2
Cozy private suite in the heart of beautiful Gardiner.
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥47,244
￥70,598 total
includes taxes & fees
Dec 1 - Dec 2
Rustic 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, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is ￥13,900
￥31,024 total
includes taxes & fees
Dec 2 - Dec 3
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Terrace/patio
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, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is ￥11,714
￥28,663 total
includes taxes & fees
Nov 30 - Dec 1
Dream getaway apartment in the foot of Gunks Ridge
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

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

Kingston
9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
The price is ￥11,878
￥44,636 total
includes taxes & fees
Dec 15 - Dec 16
Retro Retreat: renovated 2BR, desk, no chore list!
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is ￥13,353
￥36,821 total
includes taxes & fees
Dec 3 - Dec 4
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Property grounds
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Charming 2-bedroom cabin on 25 acres with loft space and full basement

Hyde Park
10.0 out of 10, Exceptional, (1)
"Great communication with the host. They thought of every detail down to a bone for our dog. Property is gorgeous with plenty of room to relax, enjoy a fire, and have hours of fun in the game room. We felt super relaxed when we walked in - like being home. "
United States
Darlene D.
The price is ￥39,045
￥60,601 total
includes taxes & fees
Dec 2 - Dec 3
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Property grounds
Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge

Stone Ridge
9.4 out of 10, Exceptional, (14)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥13,275
￥28,662 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Apartment with Sauna in Historic Stone Ridge
Exterior
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, (5)
The price is ￥15,618
￥55,795 total
includes taxes & fees
Nov 30 - Dec 1
House on the Babbling Brook- Quiet 2BR + King Bed!
3 bedrooms, iron/ironing board, travel crib, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms

2.0 star property
Holmes
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥32,017
￥91,873 total
includes taxes & fees
Dec 15 - Dec 16
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

New Paltz
9.8 out of 10, Exceptional, (10)
"Absolutely stunning A-frame! Super spacious, very clean/tidy, lots of room to hang inside, downstairs or have a fire outdoors. Beautiful area not far from New Paltz. We had such a fantastic time and would recommend this place to any group staying in the area! "
United States
Danielle O.
The price is ￥53,179
￥117,984 total
includes taxes & fees
Dec 9 - Dec 10
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
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

Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie

10/10 Excellent
"Great location and very clean. "
Kristin 1-night trip
Posted 2 days ago
Homewood 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?

The House In Highland- Secluded Retreat: Visitors like this Highland vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Our home is perfect for relaxing and having lots of fun, with near by activity’s as a favorite home for rent in Highland.

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.