Photo by throwingsofas

Highland Park Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Highland Park

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is AU$139
includes taxes & fees
9 Dec - 10 Dec
Wrigleyville Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is AU$285
includes taxes & fees
14 Dec - 15 Dec
The Gem Museum Suites

Apartment in Lakeview

9.0 out of 10, Wonderful, (39)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
The price is AU$251
includes taxes & fees
9 Dec - 10 Dec
Clean & Equipped 1BR Apt

Apartment in Lakeview

9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is AU$276
includes taxes & fees
9 Dec - 10 Dec
Lakeview 2BR Apartment

Apartment in Edgewater

9.8 out of 10, Exceptional, (37)
"Had a great stay. Great location. "
United States
Justin
The price is AU$254
includes taxes & fees
21 Dec - 22 Dec
Relaxing Chicago Studio

Condo in West Town

10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$314
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Edgewater

9.4 out of 10, Exceptional, (50)
"This property was very clean and comfortable. Easy to access and we loved the walkable neighborhood. Would recommend based on cleanliness alone. "
United States
Beth M.
The price is AU$198
includes taxes & fees
9 Dec - 10 Dec
Cozy studio in Andersonville Chicago

Apartment in East Garfield Park

7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!

Holiday Home in Waukegan

2.0 star property
10.0 out of 10, Exceptional, (2)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is AU$370
includes taxes & fees
9 Dec - 10 Dec
Home -2 bedroom, 4k projector

Apartment in Edgewater

9.6 out of 10, Exceptional, (42)
"It was quite cold in Chicago during our stay, but the apartment was nice and warm! The space is huge and the hosts were very communicative. The location is great - lots of food options and the L nearby. The apartment felt fairly clean overall, but the towels and sheets were a bit stained and the floors and doors were a bit squeaky. Overall, it is a great place to stay for a trip of any length!"
United States
Debbie
Luxurious 3 Bedroom Apartment in Chicago

Apartment in Lakeview

9.8 out of 10, Exceptional, (21)
"The apartment worked out perfectly for our stay. Very good location for our activities and comfortable for just hanging out."
United States
Linda S.
The price is AU$281
includes taxes & fees
9 Dec - 10 Dec
Beautifully Set Up 2BR Space

Condo in Lakeview

10.0 out of 10, Exceptional, (111)
"Got together for a friends reunion in Chicago. The property was perfect and had all the extras in place to make it feel like a home for a few days. I would definitely stay again and highly recommend. "
United States
Jason M.
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Apartment in Lakeview

9.0 out of 10, Wonderful, (31)
"Great stay. Place was spic and span on arrival and host very easy to communicate with. "
United States
Lukas H O.
The price is AU$281
includes taxes & fees
9 Dec - 10 Dec
Charming 2BR in Vibrant Lakeview

Holiday Home in Near North Side

9.4 out of 10, Exceptional, (106)
"Awesome space for our large group! Location couldn’t have been better - on a very nice street with tons of bars and restaurants near by."
United States
Elias P.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Holiday Home in West Town

2.0 star property
NEW to the market! Relax with family in a super Lux Custom SFH. West town.

Condo in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"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."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location

Apartment in Lakeview

9.6 out of 10, Exceptional, (170)
"Great visit! Awesome property and owners! "
United States
Matt P.
Walk to Wrigley Field/Monthly Discounts Available

Apartment in Lakeview

8.6 out of 10, Excellent, (12)
"Host communicated great and check in and check out was easy"
United States
Melanie C.
The price is AU$243
includes taxes & fees
1 Jan - 2 Jan 2026
Bright & Modern Lakeview Studio
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.
Save an average of 15% on thousands of hotels when you're signed in

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$139 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, 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?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This holiday home rental outside of Highland Park offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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.