Highland Park Vacation Rentals

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Our top choices for Highland Park vacation rentals

8.0 out of 10, Very Good, (4 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is ¥9,278
¥22,945 total
includes taxes & fees
Mar 4 - Mar 5
Chic Studio in Downtown Highland Park near Metra

Apartment in Downtown Chicago

Sleek 1BR Apartment w/ In-unit Laundry
10.0 out of 10, Exceptional, (1 review)
"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
The price is ¥15,464
¥32,756 total
includes taxes & fees
Feb 26 - Feb 27
Sleek 1BR Apartment w/ In-unit Laundry

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 out of 10, Exceptional, (5 reviews)
"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
The price is ¥15,464
¥31,209 total
includes taxes & fees
Feb 26 - Feb 27
Chic Studio in the Heart of the Gold Coast

Vacation Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is ¥10,622
¥31,989 total
includes taxes & fees
Mar 3 - Mar 4
A quiet stay while you are away

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ¥19,678
¥39,699 total
includes taxes & fees
Mar 2 - Mar 3
The Oak Park Loft

Apartment in Irving Park

Charming Sunlit 1BR Apartment
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is ¥10,670
¥27,141 total
includes taxes & fees
Mar 1 - Mar 2
Charming Sunlit 1BR Apartment

Apartment in Portage Park

Homey 2BR Apt w/ Parking
9.4 out of 10, Exceptional, (9 reviews)
"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "
United States
Sharlene T.
The price is ¥10,758
¥29,703 total
includes taxes & fees
Feb 26 - Feb 27
Homey 2BR Apt w/ Parking

Apartment in Irving Park

Chic 2BR Haven Near Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
The price is ¥10,670
¥29,460 total
includes taxes & fees
Feb 26 - Feb 27
Chic 2BR Haven Near Irving Park
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥13,778
¥39,900 total
includes taxes & fees
Feb 26 - Feb 27
2-bedroom apartment just 2 minutes drive to Wrigley Field

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (26 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ¥9,742
¥26,053 total
includes taxes & fees
Feb 26 - Feb 27
Nice 1BR Spot, Unwind & Relax

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (51 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
The price is ¥9,278
¥23,853 total
includes taxes & fees
Feb 26 - Feb 27
Relaxing Chicago Studio
8.4 out of 10, Very Good, (7 reviews)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
United States
Ever
The price is ¥11,443
¥30,558 total
includes taxes & fees
Mar 1 - Mar 2
Ideal 2BR Getaway Close to Attractions

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (431 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
9.8 out of 10, Exceptional, (77 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is ¥15,170
¥30,008 total
includes taxes & fees
Mar 5 - Mar 6
Master qtr close to nature & easy urban facilities
10.0 out of 10, Exceptional, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ¥14,691
¥19,026 total
includes taxes & fees
Feb 26 - Feb 27
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Apartment in Edgewater

Stylish and Roomy 2BR in Chicago
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
The price is ¥12,371
¥31,452 total
includes taxes & fees
Mar 4 - Mar 5
Stylish and Roomy 2BR in Chicago

Apartment in North Center

Cozy 3BR Gem in North Center
8.6 out of 10, Excellent, (14 reviews)
"Communication was great and check in was a breeze. It was exactly what we needed in a great part of town! "
United States
Russell S.
The price is ¥11,598
¥42,317 total
includes taxes & fees
Mar 2 - Mar 3
Cozy 3BR Gem in North Center

Apartment in Rogers Park

Sunlit Studio with City Charm
8.0 out of 10, Very Good, (9 reviews)
"very nice room and clean. great one night stay!"
United States
Christian B.
The price is ¥9,278
¥23,963 total
includes taxes & fees
Feb 26 - Feb 27
Sunlit Studio with City Charm
10.0 out of 10, Exceptional, (5 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is ¥17,482
¥37,946 total
includes taxes & fees
Feb 26 - Feb 27
Pine Beam Sloth Apartment next to Blue Line
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

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

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Look no further and take a look at our great range of rental properties in Highland Park!

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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This vacation home rental near Highland Park is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.