A pebbly beach with waves at sunset.

Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Highland Park vacation rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ₩266,027
₩304,562 total
includes taxes & fees
Oct 31 - Nov 1
The Gem Museum Suites
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (537 reviews)
"Beautiful property, great amenities."
United States
Erik
The price is ₩303,802
₩389,654 total
includes taxes & fees
Nov 4 - Nov 5
Level Chicago – Old Town
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ₩198,768
₩233,334 total
includes taxes & fees
Nov 3 - Nov 4
Wrigleyville Suites
Terrace/patio

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ₩256,550
₩442,347 total
includes taxes & fees
Oct 25 - Oct 26
At Home in Oak Park
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

5. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ₩215,753
₩395,621 total
includes taxes & fees
Oct 27 - Oct 28
Historic Oak Park Home
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

6. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ₩145,629
₩315,351 total
includes taxes & fees
Oct 28 - Oct 29
The Oak Park Loft
A building with a white exterior and a tree with white blossoms in front.

7. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
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

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

10/10 Excellent
"I felt very safe! The shuttle tends to arrive a bit late but overall good."
Giuliana 1-night trip
Posted 21 hours ago
Super 8 by Wyndham 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
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  • 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 where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more secluded option if you want a quieter place to stay. 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 Wrigley Field and Six Flags Great America.

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.