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
Highland Park
8.4 out of 10, Very good, (7 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$282
includes taxes & fees
15 Mar - 16 Mar
Stunning & Stylish Downtown Studio - Highland Park

Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
8.0 out of 10, Very good, (4 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AU$220
includes taxes & fees
17 Mar - 18 Mar
Chic Studio in Downtown Highland Park near Metra

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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is AU$319
includes taxes & fees
10 Mar - 11 Mar
Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is AU$253
includes taxes & fees
11 Mar - 12 Mar
Nice 1BR Spot, Unwind & Relax

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (60 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is AU$434
includes taxes & fees
10 Mar - 11 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is AU$345
includes taxes & fees
10 Mar - 11 Mar
A quiet stay while you are away

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
10.0 out of 10, Exceptional, (52 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
The price is AU$222
includes taxes & fees
11 Mar - 12 Mar
Relaxing Chicago Studio

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is AU$282
includes taxes & fees
10 Mar - 11 Mar
Uptown Studio Gem Sum

Cozy 3BR Gem in North Center

Cozy 3BR Gem in North Center
North Center
8.6 out of 10, Excellent, (14 reviews)
"Communication was great and check in was a breeze. It was exactly what we needed in a great part of town! "
United States
Russell S.
The price is AU$397
includes taxes & fees
10 Mar - 11 Mar
Cozy 3BR Gem in North Center

Modern 2BR with Reliable Wi-Fi

Modern 2BR with Reliable Wi-Fi
Lakeview
9.0 out of 10, Wonderful, (6 reviews)
"Great location for seeing a Cubs game. Easy to follow "
United States
David A.
The price is AU$349
includes taxes & fees
10 Mar - 11 Mar
Modern 2BR with Reliable Wi-Fi

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very good, (32 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is AU$326
includes taxes & fees
10 Mar - 11 Mar
Oak Park Queen

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
Lakeview
9.2 out of 10, Wonderful, (5 reviews)
"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"
United States
Matthew B.
The price is AU$447
includes taxes & fees
23 Mar - 24 Mar
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.0 out of 10, Very good, (9 reviews)
"very nice room and clean. great one night stay!"
United States
Christian B.
The price is AU$253
includes taxes & fees
10 Mar - 11 Mar
Sunlit Studio with City Charm

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is AU$471
includes taxes & fees
10 Mar - 11 Mar
Quaint Bungalow, near Great Lakes Naval Base

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is AU$178
includes taxes & fees
10 Mar - 11 Mar
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (7 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
The price is AU$358
includes taxes & fees
10 Mar - 11 Mar
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Boystown Chic 2BR Escape

Boystown Chic 2BR Escape
Lakeview
10.0 out of 10, Exceptional, (18 reviews)
"Very clean and amazing comfortable stay!!"
United States
Justin M.
The price is AU$335
includes taxes & fees
17 Mar - 18 Mar
Boystown Chic 2BR Escape

Ideal 2BR Getaway Close to Attractions

Ideal 2BR Getaway Close to Attractions
Rogers Park
8.4 out of 10, Very good, (7 reviews)
"Host was fantastic and property excellent!"
United States
David R.
The price is AU$310
includes taxes & fees
15 Mar - 16 Mar
Ideal 2BR Getaway Close to Attractions

2BR Apartment Beautifully Furnished

2BR Apartment Beautifully Furnished
Lakeview
10.0 out of 10, Exceptional, (9 reviews)
"We loved the place. The feeling of home away from home."
United States
Sataish
The price is AU$349
includes taxes & fees
10 Mar - 11 Mar
2BR Apartment Beautifully Furnished
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$165 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?

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 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.