Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
$137 nightly
The price is $146
Nov 10 - Nov 11
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.
$145 nightly
The price is $154
Dec 6 - Dec 7
Total with taxes and fees
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.
$136 nightly
The price is $144
Nov 29 - Nov 30
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra
A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (307 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
$176 nightly
The price is $201
Nov 11 - Nov 12
Total with taxes and fees
The Gem Museum Suites
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.
$179 nightly
The price is $190
Nov 10 - Nov 11
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.

6. 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 traveler
$68 nightly
The price is $76
Nov 19 - Nov 20
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

7. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (49 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
$149 nightly
The price is $174
Nov 10 - Nov 11
Total with taxes and fees
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

8. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
$234 nightly
The price is $274
Nov 23 - Nov 24
Total with taxes and fees
Level Chicago – Old Town
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

9. 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.
$211 nightly
The price is $231
Nov 16 - Nov 17
Total with taxes and fees
Well-Equipped 2BR Unit with Parking
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.

10. 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.
$74 nightly
The price is $82
Nov 19 - Nov 20
Total with taxes and fees
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,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.

11. 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
$68 nightly
The price is $76
Nov 19 - Nov 20
Total with taxes and fees
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.

12. 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
$73 nightly
The price is $80
Nov 19 - Nov 20
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
A modern living room with a flat-screen TV, a coffee table, a blue armchair, and a gray sofa.

13. The Beach Park Retreat

The Beach Park Retreat
Beach Park
10.0 out of 10, Exceptional, (1 review)
"The host, Hugo, was friendly and answered questions promptly, the apartment was spacious and well maintained. The kitchen had everything we needed for a weekend trip. I would recommend this property to anyone staying in the area."
United States
Sara
$221 nightly
The price is $244
Nov 10 - Nov 11
Total with taxes and fees
The Beach Park Retreat
A bedroom with a bed, a chair, a desk, a bathroom with a bathtub, and a shower.

14. 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
$67 nightly
The price is $75
Dec 1 - Dec 2
Total with taxes and fees
King Bed Non-Smoking
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

15. 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.
$78 nightly
The price is $87
Nov 19 - Nov 20
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

16. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (40 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
$361 nightly
The price is $412
Nov 16 - Nov 17
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A bathroom with a toilet, sink, and window with blinds.

17. 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, (4 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.
$173 nightly
The price is $187
Nov 10 - Nov 11
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

18. 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
$404 nightly
The price is $412
Nov 11 - Nov 12
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

19. 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.
$210 nightly
The price is $252
Nov 10 - Nov 11
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a blue sofa, a patterned rug, and a television.

20. 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.
$168 nightly
The price is $187
Nov 10 - Nov 11
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
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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Find vacation rentals that suit your style

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Top Highland Park Hotel Reviews

A Courtyard by Marriott hotel with a well-lit entrance, landscaped surroundings, and a modern architectural design.
Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook
Highland Park

10/10 Excellent

Will definitely stay here again!
United States
Barry
Reviewed December 3, 2023
Courtyard by Marriott Chicago Highland Park/Northbrook

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 $75 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.

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.

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