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Highland Park Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Highland Park holiday rentals

Fridge, microwave, oven, stovetop
Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
2.0 star property
Highland Park
8.8 out of 10, Excellent, (6)
"The apartment was just as advertised and fit my needs. The A/C went down the first day and the host was extremely responsive and got it fixed right away. The location is perfect and and extremely convenient. 10/10 would stay again!"
United States
Rich K.
The price is HK$537
HK$1,270 total
includes taxes & fees
4 Jan - 5 Jan
Stunning & Stylish Downtown Studio - Highland Park
Fridge, microwave, oven, stovetop
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
Highland Park
10.0 out of 10, Exceptional, (1)
The price is HK$5,004
HK$8,884 total
includes taxes & fees
3 Jan - 4 Jan
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
9.8 out of 10, Exceptional, (9)
"Good for family, enjoyed the stay"
United States
Karthik
The price is HK$6,980
HK$9,830 total
includes taxes & fees
5 Jan - 6 Jan
ENVITAE Hotel 4 Bedroom Luxury Apartments
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (17)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$537
HK$1,483 total
includes taxes & fees
5 Jan - 6 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$537
HK$1,288 total
includes taxes & fees
5 Jan - 6 Jan
Gold Coast Living: Modern Studio Unit
Interior
Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
The price is HK$490
HK$1,311 total
includes taxes & fees
6 Jan - 7 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,311 total
includes taxes & fees
7 Jan - 8 Jan
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$490
HK$1,311 total
includes taxes & fees
7 Jan - 8 Jan
Sleek 1BR Apt w/ Laundry
Iron/ironing board, travel cot, bed sheets
Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is HK$537
HK$1,492 total
includes taxes & fees
13 Jan - 14 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$490
HK$1,311 total
includes taxes & fees
4 Jan - 5 Jan
Complete 1BR Home Sum
Terrace/patio
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.0 out of 10, Wonderful, (19)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
The price is HK$504
HK$1,984 total
includes taxes & fees
3 Jan - 4 Jan
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Fridge, microwave, oven, stovetop
Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
9.6 out of 10, Exceptional, (5)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
The price is HK$484
HK$1,269 total
includes taxes & fees
4 Jan - 5 Jan
Flexhome Ukrainian Village 2BR D1
Exterior detail
Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (44)
"Great spot in a wonderful location!"
United States
Jasson R.
The price is HK$1,175
HK$3,504 total
includes taxes & fees
3 Jan - 4 Jan
Chic Urban Retreat Near Wrigley Field w/Parking
Private kitchen
The Gem Museum Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (101)
"Lovely "
United States
Duncan
The price is HK$1,305
HK$1,495 total
includes taxes & fees
28 Jan - 29 Jan
The Gem Museum Suites
Children’s area
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
West Ridge
10.0 out of 10, Exceptional, (5)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is HK$799
HK$2,359 total
includes taxes & fees
6 Jan - 7 Jan
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
Fridge, microwave, oven, stovetop
1BR Homey Apt in Irving Park

1BR Homey Apt in Irving Park

1BR Homey Apt in Irving Park
Irving Park
9.0 out of 10, Wonderful, (4)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is HK$537
HK$1,366 total
includes taxes & fees
5 Jan - 6 Jan
1BR Homey Apt in Irving Park
Exterior
Bright & Modern Apt | Steps to Lake, Train, Food

Bright & Modern Apt | Steps to Lake, Train, Food

Bright & Modern Apt | Steps to Lake, Train, Food
Edgewater
10.0 out of 10, Exceptional, (11)
"This apartment was amazing! It was spacious, quiet, comfortable, and well stocked with all the amenities. The gated parking space that goes with the apartment was a plus! We would definitely stay here again!"
United States
Sarah D.
The price is HK$991
HK$1,998 total
includes taxes & fees
14 Jan - 15 Jan
Bright & Modern Apt | Steps to Lake, Train, Food
2 bedrooms, iron/ironing board, WiFi, bed sheets
Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is HK$568
HK$1,519 total
includes taxes & fees
5 Jan - 6 Jan
Comfortable 2BR Chicago Apt
Living area
Wrigleyville Suites

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
The price is HK$799
HK$938 total
includes taxes & fees
4 Jan - 5 Jan
Wrigleyville Suites
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

Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

10/10 Excellent
"We had lunch at the Ashburn restaurant. Service and food were very good. "
Peter 2-night trip
Posted 2 days ago
Loews Chicago O'Hare Hotel

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 holiday rentals in Highland Park?

Yes, there are holiday rentals close to the most popular sights in Highland Park, or you can select a more secluded option if you're looking for a relaxing stay. 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?

Home -2 bedroom, 4k projector: This holiday home rental outside of Highland Park has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.