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Highland Holiday Rentals

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Our top choices for Highland holiday rentals

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Highland
9.8 out of 10, Exceptional, (26)
"Perfect location and stay"
United States
kareem e.
The price is NZ$560
includes taxes & fees
3 Jan - 4 Jan
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

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 NZ$667
includes taxes & fees
9 Jan - 10 Jan
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

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 NZ$427
includes taxes & fees
10 Jan - 11 Jan
TRANQUIL MOUNTAIN SOLITUDE

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (30)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is NZ$420
includes taxes & fees
6 Jan - 7 Jan
Campfire Cottage: Fireplace, fire pit & no chores!

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 NZ$288
includes taxes & fees
4 Jan - 5 Jan
Dream getaway apartment in the foot of Gunks Ridge

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

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is NZ$512
includes taxes & fees
6 Jan - 7 Jan
Retro Retreat: renovated 2BR, desk, no chore list!

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, (34)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is NZ$466
includes taxes & fees
3 Jan - 4 Jan
The Studio at the Inn at High Falls

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)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$597
includes taxes & fees
4 Jan - 5 Jan
House on the Babbling Brook- Quiet 2BR + King Bed!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$458
includes taxes & fees
5 Jan - 6 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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 NZ$310
includes taxes & fees
6 Jan - 7 Jan
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

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 NZ$399
includes taxes & fees
5 Jan - 6 Jan
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44)
"We had a great overnight stay at DJ’s Dream. Kevin was welcoming and we had the perfect quiet spot to refresh and regroup. Don’t miss the Roosevelt and Vanderbilt attractions in Hyde Park!"
United States
Jean B.
The price is NZ$341
includes taxes & fees
6 Jan - 7 Jan
Mid-Century DJ’s Dream

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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 NZ$379
includes taxes & fees
5 Jan - 6 Jan
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Natural Getaway at Lakeside Orchard Farm Retreat

Natural Getaway at Lakeside Orchard Farm Retreat
2.0 star property
Monroe
The price is NZ$391
includes taxes & fees
4 Jan - 5 Jan
Natural Getaway at Lakeside Orchard Farm Retreat

Cozy Apartment with Sauna in Historic Stone Ridge

Cozy Apartment with Sauna in Historic Stone Ridge
Stone Ridge
9.0 out of 10, Wonderful, (15)
"Clean cozy will be staying again"
United States
Michael C.
The price is NZ$271
includes taxes & fees
4 Jan - 5 Jan
Cozy Apartment with Sauna in Historic Stone Ridge

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 NZ$412
includes taxes & fees
25 Jan - 26 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is NZ$484
includes taxes & fees
13 Jan - 14 Jan
Cabin in the heart of the Hudson Valley, Cabin 3

"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 NZ$955
includes taxes & fees
5 Jan - 6 Jan
"Country outside the city " 3 bedrooms 2 full bathrooms

West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (20)
"Property owner, Elaine, was great. Property was exactly as listed, clean and cozy!"
United States
Heather H.
The price is NZ$342
includes taxes & fees
3 Jan - 4 Jan
West Wing - a unique private space w/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 NZ$532
includes taxes & fees
12 Jan - 13 Jan
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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, 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 NZ$379 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?

Our home is perfect for relaxing and having lots of fun, with near by activity’s: This highly rated holiday home rental in Highland offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Highland?

With 19 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.