A pebbly beach with waves at sunset.

Highland Park Vacation Rentals

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Highland Park vacation rentals

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.
$230 nightly
The price is $244
Jul 8 - Jul 9
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park

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
$165 nightly
The price is $175
Jun 29 - Jun 30
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by Metra

Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
8.0 out of 10, Very Good, (4 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
$170 nightly
The price is $180
Jun 29 - Jun 30
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (142 reviews)
"Perfect place to stay!"
United States
Anton
$159 nightly
The price is $182
Jul 9 - Jul 10
Total with taxes and fees
The Gem Museum Suites

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$265 nightly
The price is $303
Jun 30 - Jul 1
Total with taxes and fees
The Oak Park Loft

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
$337 nightly
The price is $357
Jul 5 - Jul 6
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"We would recommend this location and suite to anyone who has a need to visit in the greater Chicago area as apposed to staying in the city."
United States
David W.
$343 nightly
The price is $390
Jun 24 - Jun 25
Total with taxes and fees
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (38 reviews)
"Amazing !!!!! Would stay again, clean, beautiful Spot, great area !"
United States
Luka
$170 nightly
The price is $200
Jun 24 - Jun 25
Total with taxes and fees
Wrigleyville Suites

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
$627 nightly
The price is $717
Jun 29 - Jun 30
Total with taxes and fees
Oak Park Victorian by FLW Studio

Haus Of Hues: MDRN Bright Peaceful Private Apt

Haus Of Hues: MDRN Bright Peaceful Private Apt
South Evanston
9.4 out of 10, Exceptional, (22 reviews)
"Great communication. "
United States
cosmo K.
$408 nightly
The price is $463
Jun 29 - Jun 30
Total with taxes and fees
Haus Of Hues: MDRN Bright Peaceful Private Apt

Navy retreat near Naval Base-Tiki Bar,Sauna,Games

Navy retreat near Naval Base-Tiki Bar,Sauna,Games
North Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. I would definitely stay there again. "
United States
Chris G.
$687 nightly
The price is $704
Jul 20 - Jul 21
Total with taxes and fees
Navy retreat near Naval Base-Tiki Bar,Sauna,Games

Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, comfortable home in a good location. This was a great place to stay while visiting Chicago. "
United States
Pelayo M.
$515 nightly
The price is $546
Jul 8 - Jul 9
Total with taxes and fees
Wonderful in Wood Dale, right by O’Hare airport!

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
$403 nightly
The price is $427
Jun 24 - Jun 25
Total with taxes and fees
Tiny Home Retreat with hot tub

Harbor Haven/Game Room/Gym

Harbor Haven/Game Room/Gym
Winthrop Harbor
10.0 out of 10, Exceptional, (13 reviews)
"Well maintained, clean, was exactly what we needed and more. "
United States
Derek R.
Harbor Haven/Game Room/Gym

Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
10.0 out of 10, Exceptional, (3 reviews)
"Great stay was clean and in a great location overall was a good experience!"
United States
Tristan P.
$264 nightly
The price is $280
Jun 29 - Jun 30
Total with taxes and fees
Cute & Cozy, 1bd Condo Apartment/townhouse

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
$524 nightly
The price is $561
Jun 29 - Jun 30
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (495 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$272 nightly
The price is $319
Jun 29 - Jun 30
Total with taxes and fees
Level Chicago – Old Town

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.
$298 nightly
The price is $338
Jul 13 - Jul 14
Total with taxes and fees
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
$673 nightly
The price is $771
Jul 7 - Jul 8
Total with taxes and fees
Vintage Urban Retreat

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
$191 nightly
The price is $202
Jun 24 - Jun 25
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Highland Park Hotel Reviews

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 $182 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 4 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 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.