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 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.
$145 nightly
The price is $154
Dec 6 - Dec 7
Total with taxes and fees
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
$144 nightly
The price is $153
Nov 30 - Dec 1
Total with taxes and fees
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
7.8 out of 10, Good, (7 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
$139 nightly
The price is $147
Dec 6 - Dec 7
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra
A room with a desk, a chair, a TV mounted on the wall displaying various streaming services, a window with a blind, and a framed picture on the wall.

4. 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.
$186 nightly
The price is $197
Nov 18 - Nov 19
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
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay"
United States
Anonymous traveler
$68 nightly
The price is $75
Nov 19 - Nov 20
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|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, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
$66 nightly
The price is $75
Dec 1 - Dec 2
Total with taxes and fees
King Bed Non-Smoking
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (308 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
$164 nightly
The price is $188
Dec 13 - Dec 14
Total with taxes and fees
The Gem Museum Suites
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

8. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
$119 nightly
The price is $139
Nov 30 - Dec 1
Total with taxes and fees
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

9. 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.
$106 nightly
The price is $131
Dec 10 - Dec 11
Total with taxes and fees
Cozy studio in Andersonville Chicago
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

10. 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.
$230 nightly
The price is $271
Nov 17 - Nov 18
Total with taxes and fees
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.

11. 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, (10 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
$226 nightly
The price is $259
Nov 13 - Nov 14
Total with taxes and fees
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
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, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
$217 nightly
The price is $261
Nov 17 - Nov 18
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
An outdoor patio with brick flooring, a grill, and a table with chairs.

13. 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
$72 nightly
The price is $80
Nov 19 - Nov 20
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
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.
$215 nightly
The price is $235
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.

15. 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 $75
Nov 19 - Nov 20
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
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.

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

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
9.6 out of 10, Exceptional, (16 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 modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

17. 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
$417 nightly
The price is $428
Nov 30 - Dec 1
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

18. 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.
$541 nightly
The price is $579
Nov 15 - Nov 16
Total with taxes and fees
6 Kings Ping-Pong Gazebo!
An outdoor patio with brick flooring, a grill, and a table with chairs.

19. 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 $86
Nov 19 - Nov 20
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (61 reviews)
"Great apt, excellent host"
United States
Colleen B.
$236 nightly
The price is $269
Nov 29 - Nov 30
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
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 $74 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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