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Highland Holiday Rentals

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Holiday Rentals in Highland

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (9)
"We had an absolutely wonderful stay at Highland House! This beautiful property is nestled in the woods, providing a serene and peaceful environment, yet it is conveniently close to town, making it easy to access local amenities and attractions. The kitchen was a standout feature, stocked with everything you could possibly need. From a Keurig and coffee pot to a tea kettle and KitchenAid mixer, it had all the appliances and utensils necessary for cooking up a storm. The variety of pots and pans...
The House In Highland- Secluded Retreat

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok

10.0 out of 10, Exceptional, (5)
"Great place to stay and beautiful grounds. "
Studio with private pool, firepit, cabana, grill, & washer/dryer-Dogs ok

The Farm at Hyde Park

9.8 out of 10, Exceptional, (74)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (246)
"A beautiful quiet setting! "
The price is AU$527
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (301)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is AU$847
includes taxes & fees
10 Aug - 11 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is AU$523
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (71)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (176)
"Loved our stay and the house. Everything was wonderful. I will say it was a little farther than 'a walk into town' and we did Uber everywhere. Everything at the house was great - nice relaxing spot!!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (44)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is AU$375
includes taxes & fees
1 Sept - 2 Sept
Esopus Creek modern Tiny house Retreat!

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is AU$357
includes taxes & fees
14 Aug - 15 Aug
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (11)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is AU$926
includes taxes & fees
13 Aug - 14 Aug
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (26)
"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!"
The price is AU$424
includes taxes & fees
8 Aug - 9 Aug
The Studio at the Inn at High Falls

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

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

10.0 out of 10, Exceptional, (2)
"loved the discovery of Rose Hill Farm and its close proximity to Greig Farm, Tivoli, and the town of Red Hook."
The price is AU$384
includes taxes & fees
11 Aug - 12 Aug
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Magnificent Lake View

2.0 star property
Magnificent Lake View

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

10.0 out of 10, Exceptional, (7)
"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! "
The price is AU$1,651
includes taxes & fees
25 Aug - 26 Aug
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (24)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
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

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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate The House In Highland- Secluded Retreat as a favourite home for rent in Highland.

How many holiday rentals will I find in Highland?

With 20 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.