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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Chic Studio in Downtown Highland Park near Metra
8.0 out of 10, Very good, (4)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AU$238
includes taxes & fees
6 Nov - 7 Nov
Chic Studio in Downtown Highland Park near Metra
Stunning & Stylish Downtown Studio - Highland Park
2.0 star property
8.8 out of 10, Excellent, (6)
"Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood "
United States
Alissa S.
The price is AU$255
includes taxes & fees
3 Nov - 4 Nov
Stunning & Stylish Downtown Studio - Highland Park
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
10.0 out of 10, Exceptional, (1)
The price is AU$1,779
includes taxes & fees
24 Oct - 25 Oct
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
Chic Studio - In Downtown Highland Park, by Metra
8.4 out of 10, Very good, (16)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
The price is AU$224
includes taxes & fees
3 Nov - 4 Nov
Chic Studio - In Downtown Highland Park, by Metra
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (4)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is AU$631
includes taxes & fees
29 Oct - 30 Oct
4BR Corporate Suite Central and Modern
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (369)
"Friendly staff and great amenities "
United States
Bryan
The price is AU$405
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
Chic Vintage Studio in the Gold Coast
The price is AU$304
includes taxes & fees
28 Oct - 29 Oct
Chic Vintage Studio in the Gold Coast
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (10)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is AU$351
includes taxes & fees
28 Oct - 29 Oct
Twice as Nice: Chic 2BR Stay with Style & Space
The One: A 1BR Stay That Feels Like Home
9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AU$318
includes taxes & fees
3 Nov - 4 Nov
The One: A 1BR Stay That Feels Like Home
Studio Gold Coast City Living
The price is AU$304
includes taxes & fees
28 Oct - 29 Oct
Studio Gold Coast City Living
Cozy Gold Coast Studio Stay
10.0 out of 10, Exceptional, (2)
"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$304
includes taxes & fees
28 Oct - 29 Oct
Cozy Gold Coast Studio Stay
Sleek 1BR Apt w/ Laundry
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 AU$318
includes taxes & fees
3 Nov - 4 Nov
Sleek 1BR Apt w/ Laundry
Complete 1BR Home Sum
The price is AU$328
includes taxes & fees
26 Oct - 27 Oct
Complete 1BR Home Sum
1BR Gold Coast Vintage Gem
The price is AU$323
includes taxes & fees
28 Oct - 29 Oct
1BR Gold Coast Vintage Gem
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (26)
"Had a great stay. Great location. "
United States
Justin
The price is AU$250
includes taxes & fees
4 Nov - 5 Nov
Relaxing Chicago Studio
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
United States
Karigan H.
The price is AU$300
includes taxes & fees
29 Oct - 30 Oct
A quiet stay while you are away
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is AU$572
includes taxes & fees
31 Oct - 1 Nov
River West, Third Floor Chicago by 747 Lofts
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is AU$321
includes taxes & fees
24 Oct - 25 Oct
Wrigleyville Suites
Montrose Studio:Your Uptown Base
9.6 out of 10, Exceptional, (5)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
The price is AU$274
includes taxes & fees
3 Nov - 4 Nov
Montrose Studio:Your Uptown Base
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."
United States
J.T.
The price is AU$332
includes taxes & fees
18 Nov - 19 Nov
Beautifully Set Up 2BR Space
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$231 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 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.