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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (21)
"We were in town for our son’s wedding and this was the perfect location for our group. Apartment was as advertised and the host was very responsive and helpful. The rooftop provided a perfect place for some pre-wedding groom/best man photos as well."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is NZ$199
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Fridge, microwave, oven, stovetop
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, (124)
"This was our second time booking and our experience was as great as the first time. It is a convenient location to many areas around Ukraine Village. Love the space and immaculate condo. As a suggestion if you enjoy cooking bring your own spices and oil. They have everything in reference to dish ware, knives, pots/pans and glasses/cups. It was my birthday weekend and the host had a special gift for me. Very thoughtful!"
NEW LUXURY CONDO WITH PATIO DECK
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Fridge, microwave, oven, stovetop
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, (54)
"It was clean and nice."
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Fridge, microwave, oven, stovetop
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
"Relaxing, quiet and clean neighborhood. Love the retro decor. Kitchen is well equipped for those that might want to cook. A few branches were down in backyard, furniture wasn't set out yet such as outdoor dining table and chairs or gazebo, but overall property was in good condition. Thank you for a relaxing place to stay."
The price is NZ$699
per night
22 May - 23 May
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is NZ$506
per night
3 Jun - 4 Jun
Your Next Vacation Home
Private kitchen
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (145)
"Kim’s place is in a quiet neighborhood, just a couple blocks from the Roscoe Village shops and restaurants. It was also an easy 20 minute walk from shops and restaurants in the Southport area and a 30 minute walk from Wrigley Field. We had no problems parking on the street throughout our stay. If you enjoy Cubs games and a variety of restaurants and shops, all within walking distance…then this is the place for you!"
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Fridge, microwave, oven, stovetop
Chic & Historic Apartment Steps from Mag Mile
10.0 out of 10, Exceptional, (11)
"Location is very quiet yet just steps from everything. Without question we would stay here again."
Chic & Historic Apartment Steps from Mag Mile
Property grounds
The Lake House-2br/2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (19)
"This apartment was perfect for visiting our daughter at Loyola University. Very close to campus, transportation and food. The apartment was clean and had everything we needed. We would stay again!"
The Lake House-2br/2bth - 50 steps from the beach!
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"We stayed here for our daughter's graduation. It was a perfect home base for everything we needed to do. Ross was attentive and thorough in explaining everything we needed to know about the unit, garage parking was a plus, beds were comfortable...overall a great stay."
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"Convenient location. Clean, modern style. Everything was excellent!"
Wrigley/Southport Corridor Garden Oasis +parking!
Fridge, microwave, oven, dishwasher
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (61)
"We booked this apartment for a quick trip and it is just as pictured. They had so many little extras in the bathroom, just in case you forgot something! I felt horrible for the tenant under due to our heavy footed children!"
Stay in “STYLE” Apartment, close to CHI downtown
Game room
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay. We were out exploring the city for the whole weekend so we didn’t spend a lot of time actually on-site. But it was a convenient location to all the things we wanted to do. It was also great for a place to crash at the end of the days. This is a great place to operate out of especially for groups! I would recommend it."
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Fridge, microwave, oven, stovetop
Stunning 3 BR in prime Chicago location
9.8 out of 10, Exceptional, (45)
"This place is in a great location in Chicago! Plenty of space and a fun main area, brought me back to when i lived in Chicago - would definitely book this place again!!"
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop
Complete Furnished & Modern 1BR Apt
9.8 out of 10, Exceptional, (6)
"I'm going to start off with some highlights. I really liked the location. You couldn't walk two blocks without finding a cute shop or some great food. The neighborhood felt very friendly. The unit was pretty small but used the space very well. Now for a couple negative details. The unit is within 20' of the train so there are trains passing every few minutes. They are pretty loud but i personally didn't mind it much. The main frustration was the radiator in the living space. It made a sound like...
The price is NZ$301
per night
22 May - 23 May
Complete Furnished & Modern 1BR Apt
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (178)
"Beautiful and spacious unit with everything you could ask for. There were 5 of us and we had plenty of space to spread out and be comfortable. Great hospitality and Ross met us for checkin even though our flight had been delayed. Wonderful location and within walking distance of restaurants, shops and the CTA station (Howard). Would definitely stay again."
Walking distance to restaurants, shops and Lake Michigan,
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Property grounds
Hidden East Village Gem
9.6 out of 10, Exceptional, (20)
"This was a great place in a great neighborhood. A little problem with the locks but handyman was called and problem resolved in about an hour and a half."
Hidden East Village Gem
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is NZ$386
per night
26 May - 27 May
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Don't see what you're looking for?
See all available properties in Highland Park
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.

Other types of properties in Highland Park you may be interested in

Terrace/patio
Ambassador Chicago, part of JdV by Hyatt
4.0 star property
8.8 out of 10, Excellent, (1012)
"The Ambassador is one of my favorite places to stay while visiting Chicago. Though, born and raised from Chicago, the ambassador is placed in the rich and lush area in the Gold coast neighborhood in Chicago. There's plenty to do and various lovely restaurants, luxury clothing shops, beautiful architecture and transportation nearby. The hotel itself is legendary for having renowned guests in its history. Its comfortable, lively, accessible, and staff is really keen to help and serve numerous...
The price is NZ$343
per night
27 May - 28 May
Ambassador Chicago, part of JdV by Hyatt
Lobby
Claridge House
4.0 star property
8.4 out of 10, Very good, (1101)
"We really enjoyed our stay here. The staff was very friendly and helpful. The rooms were clean and spacious. "
The price is NZ$247
per night
27 May - 28 May
Claridge House
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, (1003)
"The staff were so helpful and friendly, makes me want to come back. Great customer service. "
The price is NZ$324
per night
23 May - 24 May
Marriott Chicago O'Hare
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highland Park holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highland Park. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highland Park. Seeing all the best attractions is bound to make you fall in love with Highland Park. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highland Park short-term rentals, that won’t be hard to do.

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?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This holiday home rental outside Highland Park is located in the city centre, and offers a BBQ, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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?

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 Six Flags Great America.

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.

Recent reviews of Highland Park properties
Expedia verified reviews

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

5/5 Excellent
"The Ambassador is one of my favorite places to stay while visiting Chicago. Though, born and raised from Chicago, the ambassador is placed in the rich and lush area in the Gold coast neighborhood in Chicago. There's plenty to do and various lovely restaurants, luxury clothing shops, beautiful architecture and transportation nearby. The hotel itself is legendary for having renowned guests in its history. Its comfortable, lively, accessible, and staff is really keen to help and serve numerous guests whom stay. I highly recommend for people to book and stay. Plan to comeback and stay again :)"
A verified traveller stayed at Ambassador Chicago, part of JdV by Hyatt
Posted 21 hours ago
Ambassador Chicago, part of JdV by Hyatt