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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is AU$380
includes taxes & fees
1 Dec - 2 Dec
Level Chicago – Old Town

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (66)
"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."
Wrigley/Southport Corridor Garden Oasis +parking!

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (151)
"Another wonderful Friendsgiving in a beautiful condo. Perfect kitchen for this. "
NEW LUXURY CONDO WITH PATIO DECK

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (69)
"Stay was wonderful, property manager was wonderful! Would stay here again, and definitely recommend!"
Stay in “STYLE” Apartment, close to CHI downtown

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (79)
"Great communication with owner/manager. Two train stations within walking distance. Used the garage for the extra fee, worth it since we took the train everywhere. "
Stunning 3 BR in prime Chicago location

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (69)
"This property was extremely clean and well stocked. Perfect for our family. Highly recommend. "
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (163)
"The location is close to the bus, and then easy to the Metro. It was about a 40ish min travel to the Art Institute when we were there. Roscoe Village is picturesque. There is a Starbucks at the end of the street if you want your pumpkin spice latte, but they've also got plenty of local talent- the owner of Rudy's Bakery (try the butter cookies YUM!!)-was lovely. There were plenty of other places--we just didn't have time! We arrived on Halloween; the entire neighborhood came out on their front...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field

Game room+King Bed+WiFi+Near Chicago & O’Hare

10.0 out of 10, Exceptional, (22)
"We had 5 people stay. 3 bedrooms and the two couches that fold out into beds. We hung out on the deck each night, but never ended up using the fire pit. Was a warm night anyway. Great stay. "
The price is AU$700
includes taxes & fees
1 Dec - 2 Dec
Game room+King Bed+WiFi+Near Chicago & O’Hare

Hidden East Village Gem

9.6 out of 10, Exceptional, (29)
"Perfect spot for a family. Visiting for husband’s conference. Great neighborhood and easy to get to all tourist attractions. Highly recommend. All our needs were anticipated. "
Hidden East Village Gem

Bright Garden Studio

8.6 out of 10, Excellent, (15)
"Cute place, close to Northwestern. Craig the manger was very nice and helpful! Responded to all my questions, very quickly! Would stay again for for sure!! "
The price is AU$519
includes taxes & fees
30 Nov - 1 Dec
Bright Garden Studio

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (118)
"We were a group of 20 family members coming from all over the country for a wedding just a few blocks away. There was room for everyone, plus hairdryers, ironing board, iron, etc. needed to prepare for the big day. Target and Aldi, train station, and several coffee shops and restaurants, and parks within close walking distance made this the perfect location. Everyone loved staying here. We had good weather for porch sitting, and gathering outside after dark. Very helpful and available hosts too ...
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (63)
"It was great to stay in a beautiful grey stone in Gold Coast. Better yet it is located in an excellent area, less than 1/4 mile walking distance to the lake, around the corner from Michigan Avenue shopping, the Hancock Building, the Drake, Lou Malnati's and other great restaurants, and pharmacy-- we walked to all of these places! It felt like a home away from home with the layout of the home and nice neighborhood. It was stocked up with everything one needs in the kitchen, bathrooms, bedrooms...
Prime location Historic Chicago Townhouse

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (26)
"Very nice neighborhood, walking distance to Michigan Avenue, great food options, place has everything you need, I’ll stay there again, "
Chic & Historic Apartment Steps from Mag Mile

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

10.0 out of 10, Exceptional, (34)
"Very clean and well thought out/supplied apartment on a lovely street a 30 second walk to Lake Michigan. There are 2 bedrooms, one larger master with en suite bathroom, and a second full bathroom and smaller bedroom. The unit is on the bottom floor so windows are high. Diane is friendly and responsive. The walk along the beach & out to an old lighthouse was a bonus. The street has mature trees and people walking dogs. There is a 7-11 on the corner and several restaurants walking distance. ...
The Holiday Lake House - 2br 2bth - 50 steps from the beach!

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.6 out of 10, Exceptional, (35)
"Very nice apartment. Could use more pillows (or fluffier). Just as advertised. "
Chic, Cozy home, by Blue Line Train Stop + Free parking

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (27)
"I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! "
Stunning / Spacious 6BD Home + garage - Bucktown!
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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Other types of properties in Highland Park you may be interested in

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1117)
"Room was modern and very clean, with great views of city and lake"
The price is AU$271
includes taxes & fees
8 Dec - 9 Dec
Thompson Chicago, by Hyatt

Hilton Chicago O'Hare Airport

4.0 star property
7.8 out of 10, Good, (2182)
"Convenient "
The price is AU$359
includes taxes & fees
30 Nov - 1 Dec
Hilton Chicago O'Hare Airport

Chicago Getaway Hostel

2.0 star property
8.8 out of 10, Excellent, (1131)
"A very quiet and calm atmosphere. Everything was clean and well kept. Would stay here again. "
The price is AU$111
includes taxes & fees
8 Dec - 9 Dec
Chicago Getaway Hostel
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Are there holiday rentals in Highland Park?

Yes, there are holiday rentals close to the most popular sights in Highland Park, or you can select a more secluded option if you're looking for a relaxing stay. 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 3 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?

Cultural attractions include Ravinia Park and Ravinia Pavilion, whereas Lake Michigan and Chicago Botanic Garden are a couple of picturesque spots to enjoy the outdoors. 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.