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Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Highland Park vacation rentals

A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

1. 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 ￥11,390
￥23,282 total
includes taxes & fees
Nov 4 - Nov 5
Chic Studio - In Downtown Highland Park, by Metra
A modern kitchen with white cabinets, a microwave, and a stove. There is a yellow armchair with a white pillow next to a large gray and white flower painting on the wall.

2. 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 ￥11,366
￥24,904 total
includes taxes & fees
Nov 29 - Nov 30
Stunning & Stylish Downtown Studio - Highland Park
A room with a bed, a dining table with chairs, a potted plant, and a view of a cityscape through a window.

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 ￥12,190
￥24,941 total
includes taxes & fees
Nov 9 - Nov 10
Chic Studio in Downtown Highland Park near Metra
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

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

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay"
United States
Anonymous traveler
The price is ￥10,796
￥11,944 total
includes taxes & fees
Nov 19 - Nov 20
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

5. 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 ￥16,875
￥31,243 total
includes taxes & fees
Nov 10 - Nov 11
Master qtr close to nature & easy urban facilities
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

6. 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 traveler
The price is ￥10,796
￥11,944 total
includes taxes & fees
Nov 30 - Dec 1
1 King Bed | Non-Smoking, Kitchen, Shower
A hotel lobby with a striped carpet, two leather armchairs, a small table with a lamp, and a large window.

7. 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 traveler
The price is ￥11,512
￥12,737 total
includes taxes & fees
Nov 19 - Nov 20
1 King Bed | Non-Smoking, Kitchen
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

8. 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 ￥29,813
￥76,825 total
includes taxes & fees
Nov 4 - Nov 5
6 Kings Ping-Pong Gazebo!
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

9. 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 ￥12,377
￥13,694 total
includes taxes & fees
Nov 19 - Nov 20
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A bedroom with a bed, a chair, a desk, a bathroom with a bathtub, and a shower.

10. 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 traveler
The price is ￥9,794
￥11,867 total
includes taxes & fees
Dec 2 - Dec 3
King Bed Non-Smoking
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

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

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (15 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 ￥12,440
￥13,764 total
includes taxes & fees
Dec 2 - Dec 3
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

12. 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 ￥6,586
￥39,225 total
includes taxes & fees
Nov 5 - Nov 6
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

13. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (301 reviews)
"Good breakfast"
United States
Zhaohua
The price is ￥31,197
￥35,715 total
includes taxes & fees
Dec 4 - Dec 5
The Gem Museum Suites
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

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 ￥16,229
￥35,719 total
includes taxes & fees
Nov 8 - Nov 9
Well-Equipped 2BR Unit with Parking
A living room with a flat-screen TV, a coffee table, a sofa, and a radiator.

15. Perfectly Located 1-Bedroom Unit

Perfectly Located 1-Bedroom Unit
South Evanston
10.0 out of 10, Exceptional, (4 reviews)
"The apartment was very clean and the bed was super comfortable. We slept great. We didn’t spend much time at the apartment but for our trip it was exactly what we needed. "
United States
V S.
The price is ￥11,344
￥33,376 total
includes taxes & fees
Nov 9 - Nov 10
Perfectly Located 1-Bedroom Unit
A modern kitchen with white cabinets, stainless steel appliances, and a small dining area with a table and chairs.

16. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is ￥11,842
￥41,011 total
includes taxes & fees
Nov 4 - Nov 5
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

17. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is ￥9,473
￥29,126 total
includes taxes & fees
Nov 9 - Nov 10
Great Area Logan Square Apt Games Pets - Sleeps 5
A living room with a sofa, a leather chair, a coffee table, a TV, and a mirror.

18. Charming 1BR Apt in Evanston

Charming 1BR Apt in Evanston
South Evanston
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful rooms with hardwood floors and lots of natural light. Close to fun coffee shops and restaurants. Overall a great place to stay when you're in Evanston!"
United States
Kim B.
The price is ￥11,368
￥34,966 total
includes taxes & fees
Nov 10 - Nov 11
Charming 1BR Apt in Evanston
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

19. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (50 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is ￥19,569
￥22,970 total
includes taxes & fees
Nov 5 - Nov 6
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

20. 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 ￥10,352
￥20,938 total
includes taxes & fees
Nov 23 - Nov 24
Cozy studio in Andersonville Chicago
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

Hyatt Regency Deerfield

Hyatt Regency Deerfield

8/10 Good
"For the name of Hyatt Regency sure didn't feel like it. The room were good but the hotel is outdated especially the elevators."
Kaman 1-night trip
Posted 14 hours ago
Hyatt Regency Deerfield
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

10/10 Excellent
"Clean, close to the metro, and full of character!"
Mahjar 3-night trip
Posted 2 days ago
The Chicago Hotel Collection River North

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

  • View our selection of featured holiday rentals in Highland Park
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Park while they last

Look no further and take a look at our great range of rental properties in Highland Park!

Frequently asked questions

Are there vacation rentals in Highland Park?

Yes, there are vacation rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more secluded option if you want a quieter place to stay. The shops and live music are just a few reasons why travelers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What's the top vacation rental that Highland Park has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental near Highland Park is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Highland Park?

With 5 Expedia vacation rentals, you're sure 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 vacation rentals like in Highland Park?

Vacation rentals are privately owned properties you can stay in for several days or more in Highland Park. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.