Title: Highland Vacation Rentals from $88: Search Short-Term Rentals | Expedia.com

[Highland Travel Guide](https://expedia.com/Highland.dx177657)[Hotels in Highland](https://expedia.com/Highland-Hotels.d177657.Travel-Guide-Hotels)[Flights to Highland](https://expedia.com/Cheap-Flights-To-Highland.d177657.Travel-Guide-Flights)[Things to do in Highland](https://expedia.com/Things-To-Do-In-Highland.d177657.Travel-Guide-Activities)[Car Rentals in Highland](https://expedia.com/Car-Rentals-In-Highland.d177657.Car-Rental-Guide)[Highland Vacation Packages](https://expedia.com/Highland.d177657.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=177657&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=177657&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=177657&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=177657&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highland vacation rentals

![Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/4e4fcb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Studio | Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/d6f1cd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/11a11fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn Chicago Southland I-80 & I-294 Near Casino

[](https://www.expedia.com/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

Harvey

4.2/10

(73 reviews)

"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Destin

$94 nightly

$106 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-07&endDate=2026-03-08&regionId=177657&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_177657)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CONDO)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Highland%2C+Indiana%2C+United+States+of+America&regionId=177657&latLong=41.553647%2C-87.451984&adults=2&startDate=2026-05-22&d1=2026-05-22&endDate=2026-05-25&d2=2026-05-25&lodging=APARTMENT)

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## Top Highland Hotel Reviews

![Wind Creek Southland Casino and Hotel](https://images.trvl-media.com/lodging/113000000/112060000/112051600/112051593/1fba48a9_y.jpg)

### Wind Creek Southland Casino and Hotel

10/10 Excellent

"The customer service was commendable, from the front desk attendant to the housekeeping staff. The room was very clean and the aesthetically appealing. Me and my husband will be returning to enjoy the spa."

[](https://expedia.com/Chicago-Hotels-Wind-Creek-Southland-Casino-And-Hotel.h112051593.Hotel-Information)

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"As always super nice, clean, extremely helpful. Guest ambassador Chuck - Charles the best of the best. Thanks so much "

[](https://expedia.com/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Wingate by Wyndham Tinley Park](https://images.trvl-media.com/lodging/1000000/210000/203200/203191/4446a44e_y.jpg)

### Wingate by Wyndham Tinley Park

10/10 Excellent

"The room was clean, very comfortable, and visually appealing. The staff was exceptionally friendly, courteous, and helpful. We discovered on our way to the airport that our mother had left her hearing aid in the room. Tanya at the front desk immediately had housekeeping check the room. The hearing aid was there, and Tanya put them in the mail to us (overnight delivery) that very day. Wonderful and much appreciated service!"

[](https://expedia.com/Tinley-Park-Hotels-Wingate-By-Wyndham-Tinley-Park.h203191.Hotel-Information)

![EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG](https://images.trvl-media.com/lodging/1000000/590000/582600/582513/8dba8d05_y.jpg)

### EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

10/10 Excellent

"Very clean room and a great stay"

[](https://expedia.com/Tinley-Park-Hotels-Even-Hotel-Tinley-Park-Hotel-Convention-Center.h582513.Hotel-Information)

![DoubleTree by Hilton Chicago - Alsip](https://images.trvl-media.com/lodging/1000000/30000/25600/25507/fcb66f28_y.jpg)

### DoubleTree by Hilton Chicago - Alsip

10/10 Excellent

"Good bang for your buck, very friendly and professional staff."

[](https://expedia.com/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Alsip.h25507.Hotel-Information)

![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg)

### Ameristar Casino Hotel East Chicago

10/10 Excellent

"Great"

[](https://expedia.com/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information)

![Econo Lodge South Holland - Chicago Southland](https://images.trvl-media.com/lodging/1000000/10000/4000/3986/72bd041c_y.jpg)

### Econo Lodge South Holland - Chicago Southland

10/10 Excellent

"Good "

[](https://expedia.com/Chicago-Hotels-Econo-Lodge.h3986.Hotel-Information)

![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/6279b55c_y.jpg)

### Hilton Chicago/Oak Lawn

10/10 Excellent

"The rooms was excellent "

[](https://expedia.com/Chicago-Hotels-Hilton-ChicagoOak-Lawn.h17618.Hotel-Information)

![Comfort Suites near I-80 and I-94](https://images.trvl-media.com/lodging/1000000/130000/120700/120653/09e7293e_y.jpg)

### Comfort Suites near I-80 and I-94

10/10 Excellent

"The room was great"

[](https://expedia.com/Chicago-Hotels-Comfort-Suites-Lansing.h120653.Hotel-Information)

## 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 $88 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.

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- [Vacation Homes in Highland ](https://expedia.com/Highland-Private-Vacation-Homes.d177657-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Highland ](https://expedia.com/Highland-Apartments.d177657-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Highland ](https://expedia.com/Highland-Condos.d177657-aaCondos.Travel-Guide-Accommodation)
- [Motels in Highland ](https://expedia.com/Highland-Motels.d177657-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Highland ](https://expedia.com/Highland-Cottages.d177657-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland ](https://expedia.com/Highland-Cabins.d177657-aaCabins.Travel-Guide-Accommodation)
- [RV Parks in Highland ](https://expedia.com/Highland-RV-Parks.d177657-aaRVParks.Travel-Guide-Accommodation)
- [Guest Houses in Highland ](https://expedia.com/Highland-Guest-Houses.d177657-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Highland ](https://expedia.com/Highland-Villas.d177657-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Highland ](https://expedia.com/Highland-Agritourism.d177657-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Highland ](https://expedia.com/Highland-Apart-Hotels.d177657-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Highland ](https://expedia.com/Highland-Resorts.d177657-aaResorts.Travel-Guide-Accommodation)
- [B&B in Highland ](https://expedia.com/Highland-Bed-And-Breakfast.d177657-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

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### What are vacation rentals like in Highland?

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