Highland Park Holiday Rentals

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Our top choices for Highland Park holiday rentals

1. Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
Highland Park
8.4 out of 10, Very good, (7 reviews)
"Great location, quiet area, easy walking into town for breakfast etc"
United States
Tom B.
The price is NZ$276
includes taxes & fees
6 Dec - 7 Dec
Stunning & Stylish Downtown Studio - Highland Park

2. Chic Studio - In Downtown Highland Park, by Metra

Chic Studio - In Downtown Highland Park, by Metra
Highland Park
8.4 out of 10, Very good, (16 reviews)
"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 NZ$275
includes taxes & fees
30 Nov - 1 Dec
Chic Studio - In Downtown Highland Park, by Metra

3. Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
7.8 out of 10, Good, (7 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is NZ$265
includes taxes & fees
6 Dec - 7 Dec
Chic Studio in Downtown Highland Park near Metra

4. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is NZ$370
includes taxes & fees
15 Nov - 16 Nov
Master qtr close to nature & easy urban facilities

5. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay"
United States
Anonymous traveller
The price is NZ$135
includes taxes & fees
19 Nov - 20 Nov
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

6. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is NZ$135
includes taxes & fees
1 Dec - 2 Dec
King Bed Non-Smoking

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (308 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is NZ$412
includes taxes & fees
15 Nov - 16 Nov
The Gem Museum Suites

8. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is NZ$248
includes taxes & fees
15 Nov - 16 Nov
Wrigleyville Suites

9. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is NZ$236
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago

10. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is NZ$486
includes taxes & fees
17 Nov - 18 Nov
Studio Near Wrigley • Sleeps 4 • Games • Fireplace

11. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (10 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
The price is NZ$482
includes taxes & fees
16 Nov - 17 Nov
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

12. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is NZ$469
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

13. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
9.0 out of 10, Wonderful, (16 reviews)
"Everything nice neat and clean"
United States
Anonymous traveller
The price is NZ$144
includes taxes & fees
19 Nov - 20 Nov
1 King Bed | Non-Smoking, Kitchen

14. Well-Equipped 2BR Unit with Parking

Well-Equipped 2BR Unit with Parking
North Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Super clean and easy off street parking. Thanks !"
United States
Ann N.
The price is NZ$422
includes taxes & fees
16 Nov - 17 Nov
Well-Equipped 2BR Unit with Parking

15. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Chicago
8.8 out of 10, Excellent, (17 reviews)
"Room was okay, Very basic,"
United States
Anonymous traveller
The price is NZ$135
includes taxes & fees
19 Nov - 20 Nov
1 King Bed | Non-Smoking, Kitchen, Shower

16. Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
9.6 out of 10, Exceptional, (16 reviews)
"A very good property; clean, convenient, and quiet. The only thing lacking was a coffee maker in the room."
United States
Randall W.
The price is NZ$147
includes taxes & fees
19 Nov - 20 Nov
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

17. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is NZ$777
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking

18. 6 Kings Ping-Pong Gazebo!

6 Kings Ping-Pong Gazebo!
Northbrook
8.6 out of 10, Excellent, (9 reviews)
"Hosts were great. Very accommodating to our needs and quick to respond. I will stay again!"
United States
Cj Y.
The price is NZ$1,043
includes taxes & fees
16 Nov - 17 Nov
6 Kings Ping-Pong Gazebo!

19. Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
Chicago
9.0 out of 10, Wonderful, (23 reviews)
"Pretty average for extended stay"
United States
Will B.
The price is NZ$155
includes taxes & fees
19 Nov - 20 Nov
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

20. Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (61 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is NZ$476
includes taxes & fees
29 Nov - 30 Nov
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
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.

Find holiday rentals that suit your style

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$134 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Highland Park is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Wrigley Field 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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