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Holiday Rentals in Highland

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Holiday Rentals in Highland

Apartment in 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 €375
includes taxes & fees
30 Nov - 1 Dec
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

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 €196
includes taxes & fees
30 Nov - 1 Dec
TRANQUIL MOUNTAIN SOLITUDE

Apartment in Poughkeepsie

2.0 star property
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 €235
includes taxes & fees
30 Nov - 1 Dec
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

Chalet in Gardiner

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Holiday Home in 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 €274
includes taxes & fees
18 Dec - 19 Dec
Higashi: New Paltz family home with King bed minutes to downtown

Apartment in Beacon

10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is €215
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Holiday Home in 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 €196
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Apartment in Plattekill

2.0 star property
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 €231
includes taxes & fees
30 Nov - 1 Dec
Modern Hudson Valley Retreat Near Mohonk

Holiday Home in Kingston

10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is €217
includes taxes & fees
3 Dec - 4 Dec
Campfire Cottage: Fireplace, fire pit & no chores!

Holiday Home in 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 €227
includes taxes & fees
30 Nov - 1 Dec
Cozy private suite in the heart of beautiful Gardiner.

Cabin in Fishkill

10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is €399
includes taxes & fees
1 Dec - 2 Dec
Rustic Cabin in Fishkill!

Holiday Home in 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.
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Apartment in 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 €162
includes taxes & fees
1 Dec - 2 Dec
Dream getaway apartment in the foot of Gunks Ridge

Holiday Home in 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 €250
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: renovated 2BR, desk, no chore list!

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 €207
includes taxes & fees
2 Dec - 3 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Cabin in 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 €343
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom cabin on 25 acres with loft space and full basement

Apartment in Stone Ridge

9.4 out of 10, Exceptional, (14)
"Clean cozy will be staying again"
United States
Michael C.
Cozy Apartment with Sauna in Historic Stone Ridge

Holiday Home in Highland Falls

10.0 out of 10, Exceptional, (5)
The price is €316
includes taxes & fees
30 Nov - 1 Dec
House on the Babbling Brook- Quiet 2BR + King Bed!

Holiday Home in Holmes

2.0 star property
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 €520
includes taxes & fees
15 Dec - 16 Dec
"Country outside the city " 3 bedrooms 2 full bathrooms

Chalet in 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 €668
includes taxes & fees
9 Dec - 10 Dec
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

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as €173 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 House In Highland- Secluded Retreat: This highly rated holiday home rental in Highland offers a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Our home is perfect for relaxing and having lots of fun, with near by activity’s as a favourite home for rent in Highland.

How many holiday rentals will I find in Highland?

With 18 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, Franny Reese State Park and Apple Greens Golf Course 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.