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Highland Holiday Rentals

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Holiday Rentals in Highland

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

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

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

10.0 out of 10, Exceptional, (7)
"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, (76)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

7.4 out of 10, Good, (3)
"Place was as described. Small 1 bedroom apartment right in downtown Woodstock. Great location. Space was perfect for my daughter and I. Loved the decorations."
The price is NZ$630
includes taxes & fees
27 Aug - 28 Aug
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

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

9.8 out of 10, Exceptional, (28)
"Jose has a wonderful home! Beautiful and quiet stay in a well-equipped spaced. My family had a lovely time. "
The price is NZ$560
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (46)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is NZ$398
includes taxes & fees
24 Aug - 25 Aug
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

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

10.0 out of 10, Exceptional, (302)
"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 NZ$1,017
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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 NZ$459
includes taxes & fees
19 Aug - 20 Aug
The Studio at the Inn at High Falls

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (248)
"A beautiful quiet setting! "
The price is NZ$569
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock

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

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is NZ$297
includes taxes & fees
19 Aug - 20 Aug
Cabin in the heart of the Hudson Valley, Cabin 2

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

9.6 out of 10, Exceptional, (19)
"The apartment was great. Loved the sound machine for my kids in the rooms.The moment I communicated to the host about the missing pack n play & high chair, he responded quickly & fixed the issue. We walked to some great breakfast places. We would come back!"
The price is NZ$497
includes taxes & fees
3 Sept - 4 Sept
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

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

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

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

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

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

2.0 star property
The price is NZ$390
includes taxes & fees
18 Aug - 19 Aug
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Magnificent Lake View

2.0 star property
Magnificent Lake View

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

2.0 star property
9.8 out of 10, Exceptional, (12)
"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 NZ$999
includes taxes & fees
4 Sept - 5 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
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?

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 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.