A suspension bridge over a river with autumn foliage and distant hills.

Highland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Highland vacation rentals

Paper towels

Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
$445 nightly
The price is $499
Aug 3 - Aug 4
Total with taxes and fees
Amazing 3-bedroom house with AC in adorable Highland
Terrace/patio

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, (2 reviews)
"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.
$379 nightly
The price is $424
Aug 3 - Aug 4
Total with taxes and fees
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Interior

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

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
$709 nightly
The price is $794
Aug 4 - Aug 5
Total with taxes and fees
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
$560 nightly
The price is $656
Aug 3 - Aug 4
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor spa tub

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

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (36 reviews)
"Exactly as listed, great property and host."
United Kingdom
Neil C.
$550 nightly
The price is $557
Aug 5 - Aug 6
Total with taxes and fees
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Property grounds

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (56 reviews)
"Kevin's place is lovely. Would definitely stay again when visiting the area. Great location for our needs. "
United States
Sue T.
$206 nightly
The price is $233
Aug 5 - Aug 6
Total with taxes and fees
Mid-Century DJ’s Dream
Smart TV, fireplace

Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
$228 nightly
The price is $258
Aug 17 - Aug 18
Total with taxes and fees
Private, Cozy, Clean apartment in lovely Hyde Park
Terrace/patio

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 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$239 nightly
The price is $282
Aug 3 - Aug 4
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (72 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$285 nightly
The price is $337
Aug 1 - Aug 2
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (73 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
$284 nightly
The price is $328
Aug 10 - Aug 11
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
$239 nightly
The price is $282
Aug 3 - Aug 4
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
Property grounds

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (60 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
$363 nightly
The price is $407
Aug 2 - Aug 3
Total with taxes and fees
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Smart TV

The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (36 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
$395 nightly
The price is $442
Aug 2 - Aug 3
Total with taxes and fees
The DeVita House Est. 1900
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
$623 nightly
The price is $712
Aug 3 - Aug 4
Total with taxes and fees
Chestnut on Willow Lake
Smart TV, fireplace

Mossy Moody Cabin in High Falls, NY

Mossy Moody Cabin in High Falls, NY
High Falls
9.8 out of 10, Exceptional, (20 reviews)
"Had a great fall weekend staying at the cabin. Cute place and the location was perfect for our activities in the nearby towns like Kingston and Accord."
United States
Steve H.
$470 nightly
The price is $526
Aug 2 - Aug 3
Total with taxes and fees
Mossy Moody Cabin in High Falls, NY
1 bedroom, WiFi (free)

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
$110 nightly
The price is $125
Aug 19 - Aug 20
Total with taxes and fees
2 Queen Beds | Non-Smoking, Kitchen
Terrace/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
Gardiner
9.8 out of 10, Exceptional, (19 reviews)
"Clean, comfortable cabin near New Paltz. Great views, well stocked kitchen."
United States
Heather G.
$299 nightly
The price is $303
Aug 4 - Aug 5
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Smart TV, fireplace

Inn at High Falls

Inn at High Falls
High Falls
8.6 out of 10, Excellent, (18 reviews)
"Great place for hiking!"
United States
Nancy C.
$508 nightly
The price is $569
Jul 31 - Aug 1
Total with taxes and fees
Inn at High Falls
Coffee/tea maker, fridge, oven, stovetop

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (5 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
$187 nightly
The price is $212
Aug 12 - Aug 13
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
$402 nightly
The price is $458
Aug 5 - Aug 6
Total with taxes and fees
Rustic Cabin in Fishkill!
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"This location had everything we needed, and it felt safe. Cleanliness was an A+, and amenities included great coffee, a complimentary breakfast, and parking l. Definitely will be returning to this hotel on my next trip to Poughkeepsie"
Julia L. 1-night trip
Posted 2 hours ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Highland

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Highland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 Studio at the Inn at High Falls: Visitors like this Highland vacation home rental. It is located in a rural location and offers a garden, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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, Apple Greens Golf Course and Franny Reese State Park 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.