Highland Park Holiday Rentals

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Our top choices for Highland Park holiday rentals

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 reviews)
"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 AU$238
includes taxes & fees
5 Feb - 6 Feb
Stunning & Stylish Downtown Studio - Highland Park

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
Highland Park
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,639
includes taxes & fees
24 Jan - 25 Jan
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
9.4 out of 10, Exceptional, (10 reviews)
"Good for family, enjoyed the stay"
United States
Karthik
ENVITAE Hotel 4 Bedroom Luxury Apartments

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"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 AU$248
includes taxes & fees
25 Jan - 26 Jan
Chic Studio in the Heart of the Gold Coast

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 AU$252
includes taxes & fees
26 Jan - 27 Jan
Chicago-Themed 1BR in a Central Spot near Downtown

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (414 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
Level Chicago – Old Town

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, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$285
includes taxes & fees
25 Jan - 26 Jan
Twice as Nice: Chic 2BR Stay with Style & Space

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 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AU$328
includes taxes & fees
16 Feb - 17 Feb
The One: A 1BR Stay That Feels Like Home

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (28 reviews)
"Nice place "
United States
Barry
The price is AU$258
includes taxes & fees
23 Jan - 24 Jan
Wrigleyville Suites

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 AU$324
includes taxes & fees
4 Feb - 5 Feb
Stylish Japanese-Themed 2BR Apt Close to Downtown

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is AU$263
includes taxes & fees
2 Feb - 3 Feb
Complete 1BR Home Sum

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"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 AU$252
includes taxes & fees
27 Jan - 28 Jan
Sleek 1BR Apt w/ Laundry

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
10.0 out of 10, Exceptional, (4 reviews)
"Comfortable beds, great location"
United States
Jason
The price is AU$287
includes taxes & fees
1 Feb - 2 Feb
2BR Chic & Comfortable Furnished Unit

Flexhome Ukrainian Village 2BR D2

Flexhome Ukrainian Village 2BR D2
West Town
9.4 out of 10, Exceptional, (6 reviews)
"We had no issues with our stay. I loved that the check in steps were very simple especially with being in Chicago for the first time. It was stress free. It was clean and comfortable, we would definitely stay again! "
United States
Amber
The price is AU$270
includes taxes & fees
25 Jan - 26 Jan
Flexhome Ukrainian Village 2BR D2

Majestic Modern Style|13 mins DT|4 mins Lake

Majestic Modern Style|13 mins DT|4 mins Lake
Uptown
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is AU$400
includes taxes & fees
11 Feb - 12 Feb
Majestic Modern Style|13 mins DT|4 mins Lake

Cozy 1BR in Walkable Area

Cozy 1BR in Walkable Area
Lincoln Square
9.8 out of 10, Exceptional, (9 reviews)
"This was a very nice space in a great neighborhood. The host was extremely responsive and easy to work with and we were very comfortable. I would definitely recommend this property and host."
United States
marisa g.
The price is AU$252
includes taxes & fees
26 Jan - 27 Jan
Cozy 1BR in Walkable Area

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (33 reviews)
"great stay"
United States
matt R.
The price is AU$288
includes taxes & fees
26 Jan - 27 Jan
A quiet stay while you are away

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for a concert at the aragon ballroom, it was only a block away!"
United States
Maria G.
The price is AU$336
includes taxes & fees
25 Jan - 26 Jan
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is AU$287
includes taxes & fees
4 Feb - 5 Feb
Comfortable 2BR Chicago Apt

Flexhome East Village 2BR H1

Flexhome East Village 2BR H1
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Small but great option to stay for one night "
United States
Kamille K.
The price is AU$270
includes taxes & fees
1 Feb - 2 Feb
Flexhome East Village 2BR H1
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

Find out more about Highland Park

Everything you need to know about Highland Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Park holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Highland Park holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Park. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Park holiday rentals we have selected for you start as low as AU$204 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Highland Park rentals

At Expedia, we put the best Highland Park holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Park holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy 3-bedroom house in family-oriented Melrose Park.: This holiday home rental outside of Highland Park offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Highland Park?

With 4 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.