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Highland Park Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Highland Park

Fridge, microwave, oven, stovetop
Stunning & Stylish Downtown Studio - Highland Park

Apartment in Highland Park

2.0 star property
8.8 out of 10, Excellent, (6)
"Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood "
United States
Alissa S.
$154 nightly
The price is $163
Dec 8 - Dec 9
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park
Fridge, microwave, oven, stovetop
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Vacation Home in Highland Park

10.0 out of 10, Exceptional, (1)
$1,077 nightly
The price is $1,141
Dec 8 - Dec 9
Total with taxes and fees
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
Fridge, microwave, oven, stovetop
Highland Park Family Ranch - Walk to Lake & Metra to Chicago!

Vacation Home in Highland Park

$819 nightly
The price is $868
Dec 8 - Dec 9
Total with taxes and fees
Highland Park Family Ranch - Walk to Lake & Metra to Chicago!
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
Level Chicago – Old Town
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
$187 nightly
The price is $206
Dec 11 - Dec 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
TV, offices
Complete 1BR Home Sum

Apartment in Downtown Chicago

$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Complete 1BR Home Sum
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
Terrace/patio
Majestic Modern Style|13 mins DT|4 mins Lake

Apartment in Uptown

9.4 out of 10, Exceptional, (13)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
Majestic Modern Style|13 mins DT|4 mins Lake
Fridge, microwave, oven, stovetop
1BR Homey Apt in Irving Park

Apartment in Irving Park

8.8 out of 10, Excellent, (3)
"It was wonderful and wil stay agian"
United States
Crystal P.
$154 nightly
The price is $170
Dec 10 - Dec 11
Total with taxes and fees
1BR Homey Apt in Irving Park
2 bedrooms, iron/ironing board, travel crib, WiFi
Prime Location! 2BR Near Wrigley

Apartment in Lakeview

9.6 out of 10, Exceptional, (7)
"We chose this location bsed on the proximity to Wrigley Field. It was very convenient and the place fit our needs! "
United States
Erica B.
$169 nightly
The price is $185
Dec 8 - Dec 9
Total with taxes and fees
Prime Location! 2BR Near Wrigley
Fridge, microwave, oven, stovetop
Beautifully Set Up 2BR Space

Apartment in Lakeview

9.8 out of 10, Exceptional, (21)
"The apartment worked out perfectly for our stay. Very good location for our activities and comfortable for just hanging out."
United States
Linda S.
$169 nightly
The price is $185
Dec 9 - Dec 10
Total with taxes and fees
Beautifully Set Up 2BR Space
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
$185 nightly
The price is $217
Dec 10 - Dec 11
Total with taxes and fees
Chicago Third Floor Studio by 747 Lofts
1 bedroom, iron/ironing board, travel crib, WiFi
1BR Apartment in Chicago

Apartment in North Center

8.8 out of 10, Excellent, (13)
"Awesome "
United States
Robert
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
1BR Apartment in Chicago
TV, offices
Cozy 3BR Gem in North Center

Apartment in North Center

9.4 out of 10, Exceptional, (8)
"Great place to stay and host communicated quickly when needed. Will stay again on next trip to Chicago!"
United States
Alicia
$203 nightly
The price is $222
Dec 8 - Dec 9
Total with taxes and fees
Cozy 3BR Gem in North Center
TV
Nice 1BR Spot, Unwind & Relax

Apartment in Ravenswood

9.8 out of 10, Exceptional, (24)
"Great stay"
United States
Kayla K.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Terrace/patio
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Apartment in Uptown

10.0 out of 10, Exceptional, (48)
"Clean room and the host was great with communication "
United States
Heather T.
$198 nightly
The price is $238
Dec 8 - Dec 9
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
2 bedrooms, iron/ironing board, travel crib, WiFi
2BR on N Halsted St: Lakeview Living

Apartment in Lakeview

9.4 out of 10, Exceptional, (8)
"Easy check-in process, didn’t need to carry around keys, clean place, happy with the stay"
United States
Alan V.
$169 nightly
The price is $185
Dec 8 - Dec 9
Total with taxes and fees
2BR on N Halsted St: Lakeview Living
TV, offices
Vibrant 1BR Apartment

Apartment in Lakeview

9.4 out of 10, Exceptional, (3)
"Easy check in/out. Good communication "
United States
Sherri D.
$150 nightly
The price is $165
Dec 8 - Dec 9
Total with taxes and fees
Vibrant 1BR Apartment
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

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent
"Friendly staff!"
jonna lyn 1-night trip
Posted 1 day ago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

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 $103 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 near well known points of interest in Highland Park, or you can choose a secluded option if you're looking for relaxation. 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?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This vacation home rental near Highland Park offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 Naval Base Great Lakes and Wrigley Field.

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.