A pebbly beach with waves at sunset.

Highland Park Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Highland Park vacation rentals

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.

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 AED 290
AED 638 total
includes taxes & fees
1 Nov - 2 Nov
Stunning & Stylish Downtown Studio - Highland Park
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

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 AED 290
AED 599 total
includes taxes & fees
1 Nov - 2 Nov
Chic Studio - In Downtown Highland Park, by Metra
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

3. Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
7.4 out of 10, Good, (6 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AED 253
AED 580 total
includes taxes & fees
20 Oct - 21 Oct
Chic Studio in Downtown Highland Park near Metra
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

4. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is AED 437
AED 810 total
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
An outdoor patio with brick flooring, a grill, and a table with chairs.

5. 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 AED 274
AED 304 total
includes taxes & fees
25 Oct - 26 Oct
1 King Bed | Non-Smoking, Kitchen
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

6. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
The price is AED 251
AED 303 total
includes taxes & fees
5 Oct - 6 Oct
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.

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

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
9.6 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Anonymous traveler
The price is AED 259
AED 286 total
includes taxes & fees
25 Oct - 26 Oct
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
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.

8. 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)
"Big room with a kitchen,"
United States
Anonymous traveler
The price is AED 280
AED 310 total
includes taxes & fees
25 Oct - 26 Oct
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
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)
"Good place to stay,,"
United States
Anonymous traveler
The price is AED 296
AED 328 total
includes taxes & fees
25 Oct - 26 Oct
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A rooftop terrace with a brick wall, large windows, and a metal railing.

10. 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, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AED 264
AED 986 total
includes taxes & fees
5 Oct - 6 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A room with a white desk, a white chair, a round mirror, a clock, and a lamp.

11. 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 AED 364
AED 859 total
includes taxes & fees
5 Oct - 6 Oct
Well-Equipped 2BR Unit with Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

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, (29 reviews)
"Was a great and clean place to stay.. "
United States
Ashly B.
The price is AED 264
AED 986 total
includes taxes & fees
5 Oct - 6 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (57 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is AED 443
AED 1,021 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A modern bedroom with a bed, a sofa, and a hanging plant.

14. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is AED 248
AED 533 total
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

15. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (274 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AED 708
AED 810 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
A modern living room with a sofa, a round coffee table, a TV mounted on the wall, and a bed with a headboard.

16. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time at this property! After our previous rental cancelled at the last minute, we found this gem and couldn’t have been happier. Communication was clear, check-in was easy, and the property was clean and comfortable. Thanks for a great stay!"
United States
Emily G.
The price is AED 152
AED 991 total
includes taxes & fees
14 Oct - 15 Oct
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
An outdoor patio area with a wooden fence, outdoor seating with chairs and a table, and multiple ground lamps.

17. 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, (9 reviews)
"It was a great experience! Very nice and clean place. Advertised exactly as seen. Parking was very easy and the location was great. Overall, would definitely stay again!"
United States
Sophia P.
The price is AED 443
AED 1,021 total
includes taxes & fees
29 Oct - 30 Oct
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
A modern living room with a blue sofa, a patterned rug, and a television.

18. 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 AED 231
AED 758 total
includes taxes & fees
13 Oct - 14 Oct
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern apartment with a living room, kitchen, and a large window with curtains.

19. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"Perfect uptown location. Host was very responsive. "
United States
Christopher S.
The price is AED 264
AED 986 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

20. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AED 259
AED 1,116 total
includes taxes & fees
14 Oct - 15 Oct
Sleeps 7 • Huge Projector • Designated Workspace
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Park Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"My room was clean and spacious. The cleaning staff must use a fragrance that happened to"
Stephen 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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.