Photo by Meghan hernandez

Highland Park Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Highland Park

Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
Level Chicago – Old Town
Private kitchen
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (90)
"Super nice hotel and staff "
The price is HK$1,420
HK$1,626 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
The price is HK$1,196
HK$1,793 total
includes taxes & fees
18 Oct - 19 Oct
Wrigleyville Suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
9.2 out of 10, Wonderful, (28)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
The price is HK$606
HK$1,446 total
includes taxes & fees
3 Nov - 4 Nov
Clean & Equipped 1BR Apt
2 bedrooms, iron/ironing board, travel cot, WiFi
Charming 2BR in Vibrant Lakeview
Charming 2BR in Vibrant Lakeview
9.4 out of 10, Exceptional, (20)
"This place was great! Loved my stay!"
The price is HK$684
HK$1,654 total
includes taxes & fees
20 Oct - 21 Oct
Charming 2BR in Vibrant Lakeview
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (20)
"Had a great stay. Great location. "
The price is HK$583
HK$1,343 total
includes taxes & fees
4 Nov - 5 Nov
Relaxing Chicago Studio
Fridge, microwave, oven, stovetop
Stylish 1BR in Lakeview Chicago
Stylish 1BR in Lakeview Chicago
9.0 out of 10, Wonderful, (21)
"Terrific overall stay. Great location and nice place. Highly recommend."
The price is HK$700
HK$1,575 total
includes taxes & fees
3 Nov - 4 Nov
Stylish 1BR in Lakeview Chicago
WiFi, bed sheets
Bright & Modern Lakeview Studio
Bright & Modern Lakeview Studio
9.0 out of 10, Wonderful, (10)
"The property wasn’t cleaned from the previous renters. bed unmade, dirty, all the towels were dirty and dishes still dirty"
The price is HK$700
HK$1,497 total
includes taxes & fees
3 Nov - 4 Nov
Bright & Modern Lakeview Studio
TV
Nice 1BR Spot, Unwind & Relax
Nice 1BR Spot, Unwind & Relax
10.0 out of 10, Exceptional, (17)
"Great stay"
The price is HK$560
HK$1,392 total
includes taxes & fees
4 Nov - 5 Nov
Nice 1BR Spot, Unwind & Relax
3 bedrooms, iron/ironing board, travel cot, WiFi
Sleek Style 3BR Haven - Free Parking
Sleek Style 3BR Haven - Free Parking
9.8 out of 10, Exceptional, (17)
"Lived our stay here. 3 big bedrooms, clean environment. Close to things we wanted to visit. We will stay here again for sure!"
The price is HK$700
HK$2,099 total
includes taxes & fees
22 Oct - 23 Oct
Sleek Style 3BR Haven - Free Parking
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy studio in Andersonville Chicago
Cozy studio in Andersonville Chicago
9.4 out of 10, Exceptional, (38)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is HK$583
HK$1,199 total
includes taxes & fees
22 Oct - 23 Oct
Cozy studio in Andersonville Chicago
Exterior
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (20)
"The stay lacked in shelf space as well as other amenities that could be useful. "
The price is HK$807
HK$2,163 total
includes taxes & fees
23 Oct - 24 Oct
Ground Floor Studios in Chicago by 747 Lofts
Interior
Twice as Nice: Chic 2BR Stay with Style & Space
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (9)
"Had a very nice time in Chicago!"
The price is HK$762
HK$1,745 total
includes taxes & fees
20 Oct - 21 Oct
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
Beautifully Set Up 2BR Space
Beautifully Set Up 2BR Space
10.0 out of 10, Exceptional, (14)
"Great apartment, plenty of room for 4 after a Cubs game, right by Wrigley. Would definitely stay here again for a ballgame."
The price is HK$622
HK$1,600 total
includes taxes & fees
4 Nov - 5 Nov
Beautifully Set Up 2BR Space
Terrace/patio
NEW LUXURY PENTHOUSE CONDO
NEW LUXURY PENTHOUSE CONDO
10.0 out of 10, Exceptional, (196)
"Great house with a great rooftop. "
NEW LUXURY PENTHOUSE CONDO
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment
Lakeview 2BR Apartment
9.6 out of 10, Exceptional, (17)
"The apartment was as described and the customer service was amazing! "
The price is HK$614
HK$1,572 total
includes taxes & fees
22 Oct - 23 Oct
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop
Wrigley Field/Lakeview -Entire Home- Large Groups!
Wrigley Field/Lakeview -Entire Home- Large Groups!
10.0 out of 10, Exceptional, (84)
"This property was perfect for the size of our family and was a perfect location for what we did. It's walkable to Wrigley Field and very close to a train station. It made it very convenient for us to spend a couple of days going to a ball game and going downtown. The stairs might be slightly tricky for older people but overall a great stay!"
Wrigley Field/Lakeview -Entire Home- Large Groups!
Microwave, oven, stovetop, dishwasher
Luxurious 3 Bedroom Apartment in Chicago
Luxurious 3 Bedroom Apartment in Chicago
9.4 out of 10, Exceptional, (31)
"The place was nice, clean, and in a beautiful neighborhood. "
Luxurious 3 Bedroom Apartment in Chicago
Fridge, microwave, oven, stovetop
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
8.8 out of 10, Excellent, (44)
"The location of this property could not be beat for us while we were visiting family. We would definitely stay again!"
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Exterior detail
Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/Parking
10.0 out of 10, Exceptional, (40)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
The price is HK$1,166
HK$3,492 total
includes taxes & fees
20 Oct - 21 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Park Hotel Reviews

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

10/10 Excellent
"The place is absolutely beautiful & glad I got the view room. Definitely will stay there again."
Denise 1-night trip
Posted 2 days ago
Holiday Inn Chicago North-Evanston by IHG

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
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • 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 holiday rentals in Highland Park?

Yes, we give you a choice of holiday rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What are some of the best holiday rentals that Highland Park has to offer?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This holiday home rental outside of Highland Park is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Highland Park?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.