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Highland Park Holiday Rentals

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Our top choices for Highland Park holiday rentals

2.0 star property
8.8 out of 10, Excellent, (6)
"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 NZ$342
includes taxes & fees
30 Jan - 31 Jan 2026
Stunning & Stylish Downtown Studio - Highland Park
10.0 out of 10, Exceptional, (1)
The price is NZ$1,965
includes taxes & fees
2 Jan - 3 Jan 2026
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.8 out of 10, Exceptional, (9)
"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 NZ$2,180
includes taxes & fees
5 Jan - 6 Jan 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"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 NZ$285
includes taxes & fees
18 Jan - 19 Jan 2026
Gold Coast Living: Modern Studio Unit
9.6 out of 10, Exceptional, (17)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is NZ$328
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space
2.0 star property
The price is NZ$290
includes taxes & fees
5 Jan - 6 Jan 2026
Chicago-Themed 1BR in a Central Spot near Downtown

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (407)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is NZ$291
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

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 NZ$290
includes taxes & fees
21 Jan - 22 Jan 2026
Sleek 1BR Apt w/ Laundry
2.0 star property
The price is NZ$328
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish Japanese-Themed 2BR Apt Close to Downtown

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum

Apartment in Irving Park

1BR Homey Apt in Irving Park
9.0 out of 10, Wonderful, (4)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is NZ$302
includes taxes & fees
4 Jan - 5 Jan 2026
1BR Homey Apt in Irving Park

Apartment in Edgewater

Stylish and Roomy 2BR in Chicago
9.0 out of 10, Wonderful, (12)
"It was a awesome location and clean and spacious for what we needed."
United States
porschea t.
The price is NZ$328
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish and Roomy 2BR in Chicago

Apartment in Lincoln Square

Cozy & Furnished 2BR Unit
9.0 out of 10, Wonderful, (14)
"Nice location "
United States
tom b.
The price is NZ$329
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy & Furnished 2BR Unit

Apartment in Rogers Park

Spacious 2BR Near Dining & Shops
8.4 out of 10, Very good, (7)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
United States
Ever
The price is NZ$328
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious 2BR Near Dining & Shops
9.6 out of 10, Exceptional, (7)
"We chose this location bsed on the proximity to Wrigley Field. It was very convenient and the place fit our needs! "
United States
Erica B.
The price is NZ$330
includes taxes & fees
4 Jan - 5 Jan 2026
Prime Location! 2BR Near Wrigley
2.0 star property
9.8 out of 10, Exceptional, (6)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
Chicago Third Floor Studio by 747 Lofts

Apartment in West Town

Flexhome Ukrainian Village 2BR D1
9.6 out of 10, Exceptional, (5)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
The price is NZ$281
includes taxes & fees
1 Jan - 2 Jan 2026
Flexhome Ukrainian Village 2BR D1
9.4 out of 10, Exceptional, (8)
"Easy check-in process, didn’t need to carry around keys, clean place, happy with the stay"
United States
Alan V.
The price is NZ$330
includes taxes & fees
28 Jan - 29 Jan 2026
2BR on N Halsted St: Lakeview Living
10.0 out of 10, Exceptional, (48)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is NZ$427
includes taxes & fees
13 Jan - 14 Jan 2026
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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 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$221 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, there are holiday rentals close to the most popular sights in Highland Park, or you can select a more secluded option if you're looking for a relaxing stay. 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?

Chicago Gold Coast Luxury Home Best Location walking distance to anywhere! : This holiday home rental outside of Highland Park is located on a lake, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a rooftop terrace, a garden and a selection of books so that you can immerse yourself in your holiday.

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.