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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (360)
"Great place to stay. Loved it!"
Level Chicago – Old Town

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is NZ$432
includes taxes & fees
5 Oct - 6 Oct
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is NZ$270
includes taxes & fees
2 Oct - 3 Oct
Wrigleyville Suites

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (25)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
The price is NZ$323
includes taxes & fees
2 Oct - 3 Oct
Clean & Equipped 1BR Apt

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (15)
"Had a great stay. Great location. "
The price is NZ$277
includes taxes & fees
22 Oct - 23 Oct
Relaxing Chicago Studio

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
The price is NZ$367
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR in Vibrant Lakeview

Bright & Modern Lakeview Studio

9.6 out of 10, Exceptional, (8)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is NZ$332
includes taxes & fees
6 Oct - 7 Oct
Bright & Modern Lakeview Studio

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is NZ$407
includes taxes & fees
2 Oct - 3 Oct
Ground Floor Studios in Chicago by 747 Lofts

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

9.2 out of 10, Wonderful, (7)
"Had a very nice time in Chicago!"
The price is NZ$453
includes taxes & fees
29 Oct - 30 Oct
Twice as Nice: Chic 2BR Stay with Style & Space

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (15)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is NZ$361
includes taxes & fees
21 Oct - 22 Oct
Lakeview 2BR Apartment

Stylish 1BR in Lakeview Chicago

8.6 out of 10, Excellent, (17)
"Easy to access, secure building. Unit well decorated and all the basic necessities were there. Thanks again for the great stay!"
The price is NZ$349
includes taxes & fees
6 Oct - 7 Oct
Stylish 1BR in Lakeview Chicago

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (16)
"This location was perfect for our nights in Chicago. We were within walking distance of great shopping and eating. "
The price is NZ$311
includes taxes & fees
7 Oct - 8 Oct
Nice 1BR Spot, Unwind & Relax

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (34)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is NZ$277
includes taxes & fees
6 Oct - 7 Oct
Cozy studio in Andersonville Chicago

Luxurious 3 Bedroom Apartment in Chicago

9.4 out of 10, Exceptional, (30)
"The place was nice, clean, and in a beautiful neighborhood. "
Luxurious 3 Bedroom Apartment in Chicago

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (108)
"This was a great house, location, host....made our weekend easy and enjoyable!!"
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Sleek Style 3BR Haven - Free Parking

9.6 out of 10, Exceptional, (15)
"Lived our stay here. 3 big bedrooms, clean environment. Close to things we wanted to visit. We will stay here again for sure!"
The price is NZ$510
includes taxes & fees
6 Oct - 7 Oct
Sleek Style 3BR Haven - Free Parking

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (43)
"Great place to stay when you’re in town for the Cubbies! "
The price is NZ$581
includes taxes & fees
15 Oct - 16 Oct
2-bedroom apartment just 2 minutes drive to Wrigley Field

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (84)
"We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!"
Wrigley Field/Lakeview -Entire Home- Large Groups!

2BR Fitness Pad • Private Gym • Sleeps 7

9.6 out of 10, Exceptional, (5)
"I really liked how quiet and nice it was around the area "
The price is NZ$505
includes taxes & fees
2 Oct - 3 Oct
2BR Fitness Pad • Private Gym • Sleeps 7

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
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, 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 NZ$270 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?

2BR Traveler`s Favorite • Modern and Clean: This holiday home rental outside of Highland Park offers a garden, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Highland Park?

With 6 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.