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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Stunning & Stylish Downtown Studio - Highland Park

2.0 star property
Highland Park
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.
The price is NZ$287
includes taxes & fees
17 Nov - 18 Nov
Stunning & Stylish Downtown Studio - Highland Park

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Highland Park
10.0 out of 10, Exceptional, (1)
The price is NZ$2,009
includes taxes & fees
17 Nov - 18 Nov
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

4BR Corporate Suite Central and Modern

2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "
United States
Phillip
4BR Corporate Suite Central and Modern

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Perfect pet friendly pied-à-terre! This sweet studio comes highly recommended!!!!"
United States
Brandy
The price is NZ$291
includes taxes & fees
17 Nov - 18 Nov
Gold Coast Living: Modern Studio Unit

Sleek 1BR Apt w/ Laundry

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 traveller
The price is NZ$323
includes taxes & fees
2 Dec - 3 Dec
Sleek 1BR Apt w/ Laundry

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is NZ$315
includes taxes & fees
17 Nov - 18 Nov
The One: A 1BR Stay That Feels Like Home

Premium Urban 4BR - Perfect Mix of Comfort & Location

Near North Side
10.0 out of 10, Exceptional, (1)
"Nice place, clean property, great views "
United States
Zach L.
Premium Urban 4BR - Perfect Mix of Comfort & Location

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (380)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is NZ$389
includes taxes & fees
1 Dec - 2 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Complete 1BR Home Sum

Downtown Chicago
The price is NZ$315
includes taxes & fees
17 Nov - 18 Nov
Complete 1BR Home Sum

Special Skevanston Space 2mi to Northwestern University & beach

Evanston
9.0 out of 10, Wonderful, (21)
"Was super smooth and easy, property was clean as could be and communication was excellent!"
United States
Mitchell M.
The price is NZ$382
includes taxes & fees
17 Nov - 18 Nov
Special Skevanston Space 2mi to Northwestern University & beach

Montrose Studio:Your Uptown Base

Uptown
9.8 out of 10, Exceptional, (7)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
The price is NZ$273
includes taxes & fees
1 Dec - 2 Dec
Montrose Studio:Your Uptown Base

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown
10.0 out of 10, Exceptional, (47)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is NZ$402
includes taxes & fees
18 Nov - 19 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is NZ$341
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away

Pine Beam Sloth Apartment next to Blue Line

2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4)
"The place was incredible. Looks exactly as advertised. Nice neighborhood with food and coffee within walking distance. Great atmosphere! Loved my time here"
United States
Tyler S.
Pine Beam Sloth Apartment next to Blue Line

Majestic Modern Style|13 mins DT|4 mins Lake

Uptown
9.4 out of 10, Exceptional, (11)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is NZ$390
includes taxes & fees
17 Nov - 18 Nov
Majestic Modern Style|13 mins DT|4 mins Lake

1BR Fully Equipped & Central

2.0 star property
Lakeview
10.0 out of 10, Exceptional, (1)
"Excellent location. Easy walkability to Whole Foods and restaurants. Shubas just down the road. A little confusion on checking in but all worked out great."
United States
David G.
The price is NZ$357
includes taxes & fees
30 Nov - 1 Dec
1BR Fully Equipped & Central

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."
United States
Dorde U.
The price is NZ$490
includes taxes & fees
19 Nov - 20 Nov
Getaway Near ORD With Great Local Amenities

Warm & Inviting 2BR Apt

Hermosa
10.0 out of 10, Exceptional, (4)
"Everything was great. "
United States
John C.
The price is NZ$346
includes taxes & fees
1 Dec - 2 Dec
Warm & Inviting 2BR Apt

Sunny Studio in Heart of Ravenswood

Uptown
9.4 out of 10, Exceptional, (6)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
United States
Amer
The price is NZ$260
includes taxes & fees
2 Dec - 3 Dec
Sunny Studio in Heart of Ravenswood
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

Everything you need to know about Highland Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland Park holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Park holiday rentals we have selected for you start as low as NZ$179 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland Park rentals

At Expedia, we put the best Highland Park holiday 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 holiday.

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 holiday rentals in Highland Park?

Yes, we give you a choice of holiday rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What are some of the best holiday rentals that Highland Park has to offer?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: This holiday home rental outside of Highland Park is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals are there in Highland Park?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.