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Highland Park Vacation Rentals

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Check prices for these dates

Tonight
Dec 22 - Dec 23
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Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Highland Park vacation rentals

Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (403)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Interior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is ₩87,541
₩323,053 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Chicago Third Floor Studio by 747 Lofts
Interior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
The price is ₩89,189
₩325,645 total
includes taxes & fees
Jan 1 - Jan 2, 2026
River West, Second Floor Chicago by 747 Lofts
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 Park Hotel Reviews

Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

10/10 Excellent
"Super clean. Excellent service. And nice employees "
Jonathan 3-night trip
Posted 1 day ago
Comfort Suites Chicago O'Hare Airport

Find out more about Highland Park

Search for Vacation rentals in Highland Park on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Highland Park using one of the methods below:

  • View our selection of featured Vacation rentals in Highland Park
  • Use the map to find apartments and other Vacation homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Highland Park while they last

Look no further and take a look at our great range of rental properties in Highland Park!

Frequently asked questions

Are there vacation rentals in Highland Park?

Yes, there are vacation rentals near well known points of interest in Highland Park, or you can choose a secluded option if you're looking for relaxation. The shops and live music are just a few reasons why travelers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

How many vacation rentals are there in Highland Park?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Enjoy the outdoors at Lake Michigan and Chicago Botanic Garden, or simply take in cultural attractions like Ravinia Park and Ravinia Pavilion. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are vacation rentals like in Highland Park?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland Park. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks 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 great option for family trips or small group gatherings.