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Top Holiday Rentals in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (345)
"A lot of good food options walkable distance. "
The price is £211
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (86)
"Super nice hotel and staff "
The price is £166
includes taxes & fees
23 Sept - 24 Sept
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is £132
includes taxes & fees
1 Sept - 2 Sept
Wrigleyville Suites

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (12)
The price is £166
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR in Vibrant Lakeview

Clean & Equipped 1BR Apt

8.6 out of 10, Excellent, (16)
"Good experience. Would stay there again "
The price is £153
includes taxes & fees
10 Sept - 11 Sept
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (17)
"Great place! 15 min walk to Wrigley "
The price is £153
includes taxes & fees
2 Sept - 3 Sept
Cozy, Fully Set-Up 1BR Space

Stylish 1BR in Lakeview Chicago

8.6 out of 10, Excellent, (12)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is £163
includes taxes & fees
22 Sept - 23 Sept
Stylish 1BR in Lakeview Chicago

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (8)
"Had a great stay. Great location. "
The price is £135
includes taxes & fees
30 Sept - 1 Oct
Relaxing Chicago Studio

Lakeview 2BR Apartment

9.2 out of 10, Wonderful, (12)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is £164
includes taxes & fees
2 Sept - 3 Sept
Lakeview 2BR Apartment

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (15)
"Super clean. Cozy. SAFE. Short drive to nearly every big attraction! Host was very communicative and kind!!"
The price is £147
includes taxes & fees
2 Sept - 3 Sept
Nice 1BR Spot, Unwind & Relax

Uptown Studio Gem Sum

7.0 out of 10, Good, (4)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is £145
includes taxes & fees
4 Sept - 5 Sept
Uptown Studio Gem Sum

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Homey 1BR Space Apartment

9.2 out of 10, Wonderful, (5)
"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."
The price is £147
includes taxes & fees
10 Sept - 11 Sept
Homey 1BR Space Apartment

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is £676
includes taxes & fees
30 Sept - 1 Oct
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Central Haven Escape: Stylish 3BR With Free Parking

6.8 out of 10, (6)
"The overall experience was surprisingly great. We were a little worried after reading some bad reviews because of the house smelling like smoke. It didn’t. In fact, it smelled super clean and fresh. It is a cute little, older, clean 3 bedroom apartment above a building in a downtown neighborhood. So cute!"
Central Haven Escape: Stylish 3BR With Free Parking

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is £147
includes taxes & fees
7 Sept - 8 Sept
Prime City Stay in a 1BR Apt

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (23)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is £108
includes taxes & fees
2 Sept - 3 Sept
Cozy studio in Andersonville Chicago

Bright & Modern Lakeview Studio

9.0 out of 10, Wonderful, (2)
"Host communicated great and check in and check out was easy"
The price is £156
includes taxes & fees
4 Sept - 5 Sept
Bright & Modern Lakeview Studio

Luxurious 3 Bedroom Apartment in Chicago

9.2 out of 10, Wonderful, (23)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
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

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, apart-hotels, 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 favorite 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 depends 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 £108 per night. Entering your travel dates in the search wizard you might find 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?

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar: This holiday home rental outside of Highland Park offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 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.