A pebbly beach with waves at sunset.

Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$154 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
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.
$171 nightly
The price is $181
Nov 18 - Nov 19
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park
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.
$154 nightly
The price is $163
Nov 8 - Nov 9
Total with taxes and fees
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, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
$196 nightly
The price is $208
Oct 27 - Oct 28
Total with taxes and fees
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.

5. 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
$64 nightly
The price is $71
Nov 8 - Nov 9
Total with taxes and fees
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.

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
$64 nightly
The price is $71
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
An outdoor patio with brick flooring, a grill, and a table with chairs.

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
$68 nightly
The price is $75
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed | Non-Smoking, 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)
"A very good property; clean, convenient, and quiet. The only thing lacking was a coffee maker in the room."
United States
Randall W.
$70 nightly
The price is $77
Nov 8 - Nov 9
Total with taxes and fees
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)
"Pretty average for extended stay"
United States
Will B.
$74 nightly
The price is $82
Nov 8 - Nov 9
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

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
$72 nightly
The price is $82
Oct 25 - Oct 26
Total with taxes and fees
King Bed Non-Smoking
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

11. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (289 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
$188 nightly
The price is $215
Nov 20 - Nov 21
Total with taxes and fees
The Gem Museum Suites
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

12. Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (2 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
$231 nightly
The price is $253
Oct 21 - Oct 22
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

13. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
$239 nightly
The price is $283
Nov 2 - Nov 3
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
A bedroom with a bed, a desk, 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.
$237 nightly
The price is $259
Nov 8 - Nov 9
Total with taxes and fees
Well-Equipped 2BR Unit with Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

15. 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.
$215 nightly
The price is $258
Oct 21 - Oct 22
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A living room with a white sofa, a decorative vase with a plant, a small wooden figurine, and a gold decorative piece on a white coffee table.

16. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (6 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
$367 nightly
The price is $433
Oct 21 - Oct 22
Total with taxes and fees
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A rooftop terrace with a brick wall, large windows, and a metal railing.

17. 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, (30 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
$240 nightly
The price is $289
Oct 26 - Oct 27
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (60 reviews)
"Great apt, excellent host"
United States
Colleen B.
$247 nightly
The price is $280
Oct 25 - Oct 26
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A modern living room with a blue sofa, a patterned rug, and a television.

19. 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.
$181 nightly
The price is $203
Nov 10 - Nov 11
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a sofa, a round coffee table, a TV mounted on the wall, and a bed with a headboard.

20. 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.
$295 nightly
The price is $350
Nov 5 - Nov 6
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
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 O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"The front desk lady was very helpful checking in and offer the program for an upgrade and free parking for joining!"
Edwin 1-night trip
Posted 2 hours ago
Hyatt Regency O'Hare Chicago

Find out more about Highland Park

Everything you need to know about Highland Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Park vacation 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 low season months. For more hustle and bustle, you may prefer to visit Highland Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $82 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Park rentals

At Expedia, we put the best Highland Park vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.