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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

The price is NZ$2,030
includes taxes & fees
25 July - 26 July
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking

The price is NZ$1,032
includes taxes & fees
6 Aug - 7 Aug
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is NZ$391
includes taxes & fees
6 Aug - 7 Aug
The One: A 1BR Stay That Feels Like Home

Simple, Comfy Living - Furnished 1BR Pad

8.0 out of 10, Very good, (1)
"The location is close to numerous restaurants and shops. Walking distance to a lot of cool places to go. The accommodations were good. Clean, simple and very spacious for two of us. The bed and pillows were also very comfy which is always important to me!"
The price is NZ$310
includes taxes & fees
6 Aug - 7 Aug
Simple, Comfy Living - Furnished 1BR Pad

Luxurious Lincoln Park Home: Gourmet Kitchen, City Views & Family-Friendly!

"The property is very well furnished and accommodated our extended family easily. It was very clean, quiet and a good location for our activities. The owners were quick to respond to any questions and kept us informed with check in times and procedures. We were very happy!"
The price is NZ$2,072
includes taxes & fees
6 Aug - 7 Aug
Luxurious Lincoln Park Home: Gourmet Kitchen, City Views & Family-Friendly!

Bright & Modern Lakeview Studio

8.0 out of 10, Very good, (1)
"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$330
includes taxes & fees
30 July - 31 July
Bright & Modern Lakeview Studio

Paradise 1BR Apt in Lincoln Park

Paradise 1BR Apt in Lincoln Park

Perfect Stay - Modern 2BR Unit

The price is NZ$316
includes taxes & fees
6 Aug - 7 Aug
Perfect Stay - Modern 2BR Unit

Modern & Fully Furnished 1BR Apt

The price is NZ$310
includes taxes & fees
6 Aug - 7 Aug
Modern & Fully Furnished 1BR Apt

Elegant 2BR Apartment w/ In-Unit Laundry

The price is NZ$320
includes taxes & fees
12 Aug - 13 Aug
Elegant 2BR Apartment w/ In-Unit Laundry

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

6.0 out of 10, (2)
"A nice clean place with good communication"
Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Comfy 2BR in Heart of Lakeview

8.0 out of 10, Very good, (1)
"The location is very convenient—just a 15-minute walk from Boystown and 6 minutes from some great breakfast spots. One mattress should be replaced, as it is quite worn. Everything else was fine. I'm not a big fan of noisy window AC units, especially since I’m a light sleeper; even with earplugs, the noise was still bothersome. The lockbox for the key is a bit tricky—I imagine others might find it difficult to open as well. Overall, the place was more affordable than other options, so I’d give...
The price is NZ$349
includes taxes & fees
12 Aug - 13 Aug
Comfy 2BR in Heart of Lakeview

Urban Comfort • 2BR in West Town

10.0 out of 10, Exceptional, (1)
"Very clean. Host was exceptionally communicative. Would stay again!"
The price is NZ$340
includes taxes & fees
29 July - 30 July
Urban Comfort • 2BR in West Town

Spacious 4BR Retreat - Chase E1

2.0 out of 10, (1)
"3 hours before we were supposed to check-in they canceled. They had my cell phone and didn't contact me. I had messaged them to get check in information and was only told at that time the place was now unavailable. For something as important as cancelling last minute they should have called, messaged and emailed. They had no problem requiring me via my cell phone to give them not only give them the names and ages of every guest staying but a picture of my passport and CC. Was this just a scam to...
The price is NZ$345
includes taxes & fees
28 July - 29 July
Spacious 4BR Retreat - Chase E1

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (1)
"Clean, comfortable, and would definitely stay again!"
Great Layout – Spacious 2BR Apt

Sleek Style 3BR Haven - Free Parking - Ashland 2N

9.4 out of 10, Exceptional, (3)
"Centrally located "
The price is NZ$411
includes taxes & fees
6 Aug - 7 Aug
Sleek Style 3BR Haven - Free Parking - Ashland 2N

Chic apartment with fitness room and AC in beautiful Chicago

The price is NZ$508
includes taxes & fees
5 Aug - 6 Aug
Chic apartment with fitness room and AC in beautiful Chicago

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (13)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is NZ$282
includes taxes & fees
28 July - 29 July
Cozy studio in Andersonville Chicago

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (2)
"Everything was as described, clean and enjoyable, had everything you might need. Its not the biggest studio, but they did a good job with the space. Its great for the price. "
The price is NZ$312
includes taxes & fees
11 Aug - 12 Aug
Relaxing Chicago Studio

Vibrant 1BRApt in Roscoe Village

The price is NZ$310
includes taxes & fees
29 July - 30 July
Vibrant 1BRApt in Roscoe Village
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

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?

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits: This highly rated holiday home rental in Highland Park offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Highland Park?

With 4 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.