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Highland Vacation Rentals

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Vacation Rentals in Highland

3-bedroom and 2 bath cottage across Waterfall

The price is ¥47,674
¥69,648 total
includes taxes & fees
Aug 1 - Aug 2
3-bedroom and 2 bath cottage across Waterfall

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 ¥22,243
¥38,233 total
includes taxes & fees
Jul 11 - Jul 12
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 ¥84,234
¥136,319 total
includes taxes & fees
Jul 14 - Jul 15
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 ¥40,216
¥61,168 total
includes taxes & fees
Jul 21 - Jul 22
Rustic Cabin in Fishkill!

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 ¥58,496
¥84,581 total
includes taxes & fees
Jul 17 - Jul 18
Chestnut on Willow Lake

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is ¥62,152
¥89,429 total
includes taxes & fees
Jul 21 - Jul 22
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is ¥58,496
¥85,572 total
includes taxes & fees
Jul 17 - Jul 18
Red Cottage - Lakeside Property!

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

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, (11)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is ¥62,518
¥112,169 total
includes taxes & fees
Jul 14 - Jul 15
Spacious New Luxurious holiday house in lovely Hudson Valley

Rhinebeck Inn Suite with a Private Deck

The price is ¥40,699
¥52,176 total
includes taxes & fees
Jul 29 - Jul 30
Rhinebeck Inn Suite with a Private Deck

Historic Hudson Valley Estate

The price is ¥146,094
¥226,552 total
includes taxes & fees
Jul 14 - Jul 15
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 ¥76,776
¥125,249 total
includes taxes & fees
Jul 13 - Jul 14
Modern Converted Barn with Hot Tub!

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

9.8 out of 10, Exceptional, (22)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is ¥37,876
¥48,803 total
includes taxes & fees
Jul 13 - Jul 14
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 ¥65,808
¥120,932 total
includes taxes & fees
Jul 14 - Jul 15
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 ¥28,629
¥49,341 total
includes taxes & fees
Jul 29 - Jul 30
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 ¥29,021
¥51,813 total
includes taxes & fees
Aug 4 - Aug 5
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 ¥82,041
¥166,331 total
includes taxes & fees
Jul 17 - Jul 18
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 ¥47,528
¥91,533 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is ¥17,695
¥52,070 total
includes taxes & fees
Jul 29 - Jul 30
Cozy Escape -Strong Wi-Fi -Prime Location

Family friendly Spacious 4 bedroom 3 bathroom getaway

10.0 out of 10, Exceptional, (4)
"Very easy checkin, great communication from owner. Bring your own travel soap shampoo etc. Store was right down the road for these things so not a big deal. Would rent again in a heartbeat."
The price is ¥44,857
¥74,390 total
includes taxes & fees
Jul 22 - Jul 23
Family friendly Spacious 4 bedroom 3 bathroom getaway
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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Frequently asked questions

Can I find vacation rentals in Highland?

Yes, we offer vacation rentals close to the most popular points of interest in Highland, or you can select a more remote option if you want a relaxing place to stay. Highland is known for its riverfront and mountain views.

What are some of the best vacation home rentals in Highland?

The House In Highland- Secluded Retreat: Visitors like this Highland vacation home rental. It offers a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Our home is perfect for relaxing and having lots of fun, with near by activity’s as a favorite home for rent in Highland.

How many vacation rentals will I find in Highland?

With 21 Expedia vacation rentals, you're sure 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 vacation rentals like in Highland?

Vacation rentals are privately owned properties you can book for a couple days or more in Highland. Vacation rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.