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Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Highland Park

Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is NT$3,738
NT$4,388 total
includes taxes & fees
Nov 24 - Nov 25
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is NT$5,677
NT$6,500 total
includes taxes & fees
Nov 23 - Nov 24
The Gem Museum Suites
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is NT$1,978
NT$4,357 total
includes taxes & fees
Nov 30 - Dec 1
River West, Third Floor Chicago by 747 Lofts
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior
Historic Oak Park Home

Apartment in Oak Park

2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
House (2 Bedrooms) | Interior
Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Cottage in South Evanston

3.0 star property
Pet-friendly Abode, 2 Mi to Dtwn Evanston!
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Great place, get rid of Rental Car and walk to Terminal in the morning. Really convenient. Hotel remains clean and updated."
Brian 1-night trip
Posted 1 day ago
Hilton Chicago O'Hare Airport

Find out more about Highland Park

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

  • View our selection of featured holiday rentals in Highland Park
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  • Enter your travel dates to view the best deals on holiday 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.