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Highland Vacation Rentals

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Vacation Rentals in Highland

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Porter
9.0 out of 10, Wonderful, (12)
"Great pool hostess was very helpful"
United States
regina
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Creekside Cozy 3BD • Near Dunes

Valparaiso
9.0 out of 10, Wonderful, (10)
"The apartment quiet and clean and in a very nice and safe neighborhood. It fit our needs nicely for a family of four."
United States
Jason C.
$282 nightly
The price is $315
Nov 18 - Nov 19
Total with taxes and fees
Creekside Cozy 3BD • Near Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Porter
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
$136 nightly
The price is $152
Nov 16 - Nov 17
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Cozy Charm Studio Apt in Chicago

Hyde Park
10.0 out of 10, Exceptional, (1)
$143 nightly
The price is $158
Dec 3 - Dec 4
Total with taxes and fees
Cozy Charm Studio Apt in Chicago

Bright & Cozy 1BR Near UChicago

Hyde Park
10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
$162 nightly
The price is $179
Nov 18 - Nov 19
Total with taxes and fees
Bright & Cozy 1BR Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
$147 nightly
The price is $163
Dec 2 - Dec 3
Total with taxes and fees
Modern Studio Near UChicago

Charming 1BR/1BA Apt in Chicago

Hyde Park
10.0 out of 10, Exceptional, (1)
$153 nightly
The price is $168
Dec 9 - Dec 10
Total with taxes and fees
Charming 1BR/1BA Apt in Chicago

Studio Apt Comfy & Sunlit

Hyde Park
10.0 out of 10, Exceptional, (2)
"It was a great place for our in and out days in Hyde Park. "
United States
Steven
$159 nightly
The price is $176
Dec 3 - Dec 4
Total with taxes and fees
Studio Apt Comfy & Sunlit

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (1)
"Unit was convenient to our son’s home. Comfortable home. All the necessities were provided. "
United States
Michelle F.
$140 nightly
The price is $155
Dec 1 - Dec 2
Total with taxes and fees
Studio Unit | Chic + Prime Location

Contemporary 2BR Apartment in Vibrant Hyde Park

Hyde Park
10.0 out of 10, Exceptional, (1)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
$190 nightly
The price is $209
Nov 17 - Nov 18
Total with taxes and fees
Contemporary 2BR Apartment in Vibrant Hyde Park

Chic Retreat: Cozy 1BR Apartment

Hyde Park
9.0 out of 10, Wonderful, (6)
"Very quiet and comfortable. Right in the heart of Hyde Park. 10 min walk to Lake Michigan.Clean and well suited for your needs. Would gladly stay again!"
United States
Harold M.
$153 nightly
The price is $168
Dec 10 - Dec 11
Total with taxes and fees
Chic Retreat: Cozy 1BR Apartment

Sleek & Functional 2-Bedroom Apt

Hyde Park
9.6 out of 10, Exceptional, (4)
"My daughter lives in an apartment across the street from this apartment, which is why we selected this property. Hyde Park in Chicago is pretty safe and very walkable. Parking is difficult! This property was clean, but needs some updated flooring. It was very difficult to control hot water. It was extremely hot!! If you have children in this property I would recommend keeping them from turning on the hot water by themselves. The building, likely built in 1920s had been updated but is...
United States
Larri
$168 nightly
The price is $183
Dec 3 - Dec 4
Total with taxes and fees
Sleek & Functional 2-Bedroom Apt

Bright & Modern 1BR in Hyde Park

Hyde Park
10.0 out of 10, Exceptional, (1)
"Great place to stay. It was easy to settle in and relax after a long day of traveling. The bed was comfortable and great to sleep on. Will definitely try for this property again if I need to come to the area."
United States
Michael S.
$162 nightly
The price is $179
Dec 9 - Dec 10
Total with taxes and fees
Bright & Modern 1BR in Hyde Park

Plant MOOD2! FREE STREET PARKING & Wi-Fi!

Hammond
10.0 out of 10, Exceptional, (2)
"It was a great experience!!! Very clean and decorated very beautiful. The host is very friendly and responds fast."
United States
Alexis L.
$178 nightly
The price is $199
Nov 20 - Nov 21
Total with taxes and fees
Plant MOOD2! FREE STREET PARKING & Wi-Fi!

Trendy Studio Apartment in Chicago

Hyde Park
7.0 out of 10, Good, (2)
"The room was very comfortable, and the location was great for walking to the University of Chicago campus. "
United States
David M.
$149 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees
Trendy Studio Apartment in Chicago

Furnished 3BR Apt w/ Laundry

Hyde Park
9.6 out of 10, Exceptional, (4)
"It was a great stay. Everything was clean and organized. The check-in process was very smooth. The host had outstanding communication. Thank you again. "
United States
corey k.
$202 nightly
The price is $221
Nov 16 - Nov 17
Total with taxes and fees
Furnished 3BR Apt w/ Laundry

Beautiful Rustic Cabin for Two!

Griffith
9.8 out of 10, Exceptional, (16)
"We had a very nice stay. The cabin was quite cozy and comfortable."
United States
Jeremy & Rebecca F.
$92 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Soothing studio with AC/Heat in charming Hammond

2.0 star property
Hammond
$134 nightly
The price is $150
Nov 20 - Nov 21
Total with taxes and fees
Soothing studio with AC/Heat in charming Hammond

Explore Hyde Park: 2BR Apt on Blackstone Ave

Hyde Park
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
$190 nightly
The price is $209
Dec 3 - Dec 4
Total with taxes and fees
Explore Hyde Park: 2BR Apt on Blackstone Ave

Pleasant 3-bedroom house in Sauk Village

2.0 star property
Sauk Village
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
United States
Aaron K.
$125 nightly
The price is $134
Nov 23 - Nov 24
Total with taxes and fees
Pleasant 3-bedroom house in Sauk Village
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

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 $103 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.

Frequently asked questions

Are there vacation rentals in Highland?

Yes, you can find vacation rentals close to top points of interest in Highland, or you can select a more secluded option if you're looking for relaxation. Highland is known for its churches and basketball games. Make sure you have time to check out the lake views while you're in the area.

What are some of the best vacation rentals in Highland?

LakeHouse: This vacation home rental near Highland is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease 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 and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Highland?

Indiana Dunes National Park and Hoosier Prairie are a couple of lovely local spots to get outside and enjoy nature. Purdue University Northwest and Hard Rock Casino Northern Indiana are a couple of places you'll find in the larger area.

What are vacation rentals like in Highland?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip.