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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (6)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is AU$268
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (11)
"The place was extremely simple and easy. The check in was really easy, the place was very affordable, the place was extremely clean, the house owner was really easy to get a hold of and fast with answering questions. Overall a great experience!"
The price is AU$674
per night
8 May - 9 May
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (45)
"This is one of the most charming vrbo that i have stayed at. the house is just as 1 described My son graduated Navy Bootcamp and it was so nice to have the comfort of this home vs sharing 3 hotel rooms."
The price is AU$481
per night
12 May - 13 May
Quaint Bungalow, near Great Lakes Naval Base
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Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.8 out of 10, Exceptional, (7)
"It was a little dated but cozy"
The price is AU$333
per night
2 May - 3 May
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.2 out of 10, Wonderful, (15)
"we were a group of seven, aged 18 months to 66 years. the flat was great. with the three bedrooms, queen beds in two rooms, two twins in the other, plus a pack’n play for the youngest, everyone had a comfortable place to sleep. also great that we were able to make breakfast in the mornings! the neighborhood was fantastic! very friendly people, so quiet, plenty of on street parking (no permits required!!!) easy communication with the host. great price! we appreciated the welcome booklet. flat was...
The price is AU$698
per night
2 May - 3 May
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.2 out of 10, Wonderful, (9)
"This location worked out great for us. We used the kitchen each day and everyone was comfortable. Would definitely stay again."
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (7)
"Great little home away from home. Definitely need to be painted and maintenance upgrades need to be addressed but other than that we had a great time"
The price is AU$279
per night
9 May - 10 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (206)
"Nice"
The price is AU$597
per night
7 May - 8 May
Level Chicago – Old Town
Modern Luxe home w/Gameroom and Electric Fireplace
8.4 out of 10, Very good, (6)
"We really loved our stay at this house with group of our friends. This place was just perfect, newly renovated and exactly looked like it is in pictures. The house has everything needed from games in basement to the cozy beds to rest at night. Host was incredibly responsive and made us feel right at home. Recommended nearby places to explore and we had a great getaway overall. I would stay here again when in town. 10/10!!"
Modern Luxe home w/Gameroom and Electric Fireplace
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (183)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is AU$116
per night
2 May - 3 May
WoodSpring Suites Chicago Addison
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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.

Other types of properties in Highland Park you may be interested in

Ambassador Chicago, part of JdV by Hyatt
4.0 star property
8.8 out of 10, Excellent, (1001)
"Didn’t like my steak .I asked for it medium I got medium well and that lava cake was not good at all taste like it was frozen and reheated needs to be taken off the menu and replaced with a great tasting chocolate cake or a simple ice cream "
The price is AU$292
per night
14 May - 15 May
Ambassador Chicago, part of JdV by Hyatt
SpringHill Suites Chicago O'Hare by Marriott
3.0 star property
8.4 out of 10, Very good, (1002)
"The gentleman who checked me was very nice. Gave me a small card with information about breakfast hours, workout room hours, etc. This was very helpful! Thank you! Breakfast, coffee, room, and hotel great value for the stay! Clean!"
The price is AU$185
per night
5 May - 6 May
SpringHill Suites Chicago O'Hare by Marriott
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, (1002)
"The shuttle bus was wonderful! So easy to get to and from the airport. And, considering that this is an airport hotel, it was really nice and quiet!"
The price is AU$307
per night
10 May - 11 May
Marriott Chicago O'Hare
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.

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$116 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?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This holiday home rental outside Highland Park is located in the city centre, and offers a BBQ, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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?

Cultural attractions include Ravinia Park and Ravinia Pavilion, whereas Lake Michigan and Chicago Botanic Garden are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Naval Base Great Lakes and Six Flags Great America.

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.

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