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Highland Holiday Rentals

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Holiday Rentals in Highland

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is NZ$430
includes taxes & fees
24 July - 25 July
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

The George is an elegant restored home in the Hudson Valley

9.0 out of 10, Wonderful, (4)
"Nice big house in a quiet location. "
The price is NZ$1,559
includes taxes & fees
30 July - 31 July
The George is an elegant restored home in the Hudson Valley

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is NZ$701
includes taxes & fees
11 Aug - 12 Aug
Rustic Cabin in Fishkill!

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is NZ$1,009
includes taxes & fees
14 Aug - 15 Aug
Hickory on Willow Lake

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is NZ$969
includes taxes & fees
24 July - 25 July
Chestnut on Willow Lake

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is NZ$417
includes taxes & fees
25 July - 26 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Spacious New Luxurious holiday house in lovely Hudson Valley

10.0 out of 10, Exceptional, (12)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is NZ$1,257
includes taxes & fees
30 July - 31 July
Spacious New Luxurious holiday house in lovely Hudson Valley

Rhinebeck Inn Suite with Private Deck

2.0 star property
The price is NZ$586
includes taxes & fees
3 Aug - 4 Aug
Rhinebeck Inn Suite with Private Deck

Cozy Rhinebeck Inn Suite

10.0 out of 10, Exceptional, (2)
The price is NZ$537
includes taxes & fees
31 July - 1 Aug
Cozy Rhinebeck Inn Suite

Rhinebeck Inn Suite with Private Living Room

The price is NZ$581
includes taxes & fees
31 July - 1 Aug
Rhinebeck Inn Suite with Private Living Room

Rhinebeck Inn Suite with a Private Deck

The price is NZ$638
includes taxes & fees
31 July - 1 Aug
Rhinebeck Inn Suite with a Private Deck

Rhinebeck Inn Suite with Private Deck and Fire Pit

The price is NZ$608
includes taxes & fees
4 Aug - 5 Aug
Rhinebeck Inn Suite with Private Deck and Fire Pit

Historic Hudson Valley Estate

The price is NZ$2,594
includes taxes & fees
3 Aug - 4 Aug
Historic Hudson Valley Estate

Modern Converted Barn with Hot Tub!

10.0 out of 10, Exceptional, (4)
"The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property."
The price is NZ$1,436
includes taxes & fees
28 July - 29 July
Modern Converted Barn with Hot Tub!

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

9.8 out of 10, Exceptional, (26)
"Plenty of room for my family"
The price is NZ$588
includes taxes & fees
27 July - 28 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is NZ$1,378
includes taxes & fees
30 July - 31 July
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is NZ$582
includes taxes & fees
4 Aug - 5 Aug
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is NZ$586
includes taxes & fees
20 Aug - 21 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is NZ$2,102
includes taxes & fees
14 Aug - 15 Aug
Room for Everyone: Spacious 6BR West Point Retreat

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is NZ$1,043
includes taxes & fees
3 Aug - 4 Aug
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
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 21 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.