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Highland Park Holiday Rentals

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Holiday Rentals in Highland Park

Modern Luxe home w/Gameroom and Electric Fireplace
Private kitchen
Modern Luxe home w/Gameroom and Electric Fireplace
8.4 out of 10, Very good, 6 reviews
"We really loved our stay at this house with group of our friends. This place was just perfect, newly renovated and exactly looked like it is in pictures. The house has everything needed from games in basement to the cozy beds to rest at night. Host was incredibly responsive and made us feel right at home. Recommended nearby places to explore and we had a great getaway overall. I would stay here again when in town. 10/10!!"
Modern Luxe home w/Gameroom and Electric Fireplace
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 211 reviews
"Loved all the neighborhood dogs & farmers market"
The price is HK$2,348
HK$2,889 total
includes taxes & fees
16 Jun - 17 Jun
Level Chicago – Old Town
WoodSpring Suites Chicago Addison
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 188 reviews
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is HK$704
HK$746 total
includes taxes & fees
5 Jun - 6 Jun
WoodSpring Suites Chicago Addison
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Walking distance to restaurants, shops and Lake Michigan,
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 9 reviews
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is HK$1,275
HK$1,622 total
includes taxes & fees
5 Jun - 6 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, 39 reviews
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, 22 reviews
"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
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, 7 reviews
"Easy to check in, good information for parking in the area. The place was clean and nice."
Ground Floor Studios in Chicago by 747 Lofts
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, 71 reviews
"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
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, 126 reviews
"It will be interesting to see how the balcony in the living room will be incorporated into the final apartment…."
NEW LUXURY CONDO WITH PATIO DECK
Stay in “STYLE” Apartment, close to CHI downtown
Fridge, microwave, oven, dishwasher
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, 62 reviews
"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
Beautiful, Remodeled Penthouse Unit in Old Town!
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, 7 reviews
"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!
Hidden East Village Gem
Property grounds
Hidden East Village Gem
9.6 out of 10, Exceptional, 21 reviews
"Property was clean and spacious which was perfect for our family of 4. The neighbor was cute and we felt safe being there. Free street parking, though spaces were some times limited. Overall, we were happy with our stay."
Hidden East Village Gem
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
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, 57 reviews
"Thank you so much for the lovely stay. Although I was unable to attend, my husband, son, daughter, and son-in-law were able to stay. They all made mention of how clean everything was, how everything was comfortable and well appointed. It was easy to check in and check out. I think beds could have been a little bit softer (all four commented on that), but your place is beautiful! Would also recommend ceiling fans or floor fans in each room to cut out noise and for better temperature. Would...
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Games room
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, 8 reviews
"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)
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop
Stunning 3 BR in prime Chicago location
9.8 out of 10, Exceptional, 45 reviews
"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
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Fridge, microwave, oven, stovetop
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, 44 reviews
"Communication was fantastic. Location is excellent. I stayed there with my wife and kids and there was plenty of room. Would be great for a big group of friends or a bachelor party weekend."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Bright Garden Studio
Interior
Bright Garden Studio
9.0 out of 10, Wonderful, 4 reviews
"I'm a seminary student, and I came into town for an intensive class. So, I was really only in the space in the evenings, but it was comfy. The location is amazing!!! The studio apartment was decently clean. The projector is VERY cool. There were a few details I could not find instructions for, like where to take the garbage out when I was on my way out. But I left a message for the owner and they were good about it. I would stay again. Recommend."
Bright Garden Studio
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Private kitchen
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, 147 reviews
"We had an excellent stay. The location was perfect for us. We walked to Wrigley Field to watch a couple games. The accommodation is super close to hop onto the train to get us downtown and to the airport. Great neighborhood. Bartolommeo Pizza just around the corner, excellent pizza. The suite is exactly as it is in the photos. Very comfortable with everything we needed. Would definitely book again."
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Fridge, microwave, oven, stovetop
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, 14 reviews
"Host was amazing with communication, check in was seemless house was clean and a great experience for me and my family would high recommend"
The price is HK$2,052
HK$3,842 total
includes taxes & fees
23 Jun - 24 Jun
Game room/King Bed /Wi-Fi/Deck + Fire Pit
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

Claridge House
Lobby
Claridge House
4.0 star property
8.4 out of 10, Very good, 1,114 reviews
"Great hotel!"
The price is HK$1,197
HK$1,635 total
includes taxes & fees
16 Jun - 17 Jun
Claridge House
Best Western At O'Hare
Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, 1,878 reviews
"Value of money "
The price is HK$924
HK$1,053 total
includes taxes & fees
1 Jul - 2 Jul
Best Western At O'Hare
Marriott Chicago O'Hare
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, 1,012 reviews
"My children, and I stayed here recently, and this hotel is absolutely gorgeous!! & was very clean! The shrimp from their restaurant was delicious along with the quesadillas! "
The price is HK$1,243
HK$1,460 total
includes taxes & fees
1 Jul - 2 Jul
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.

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:

  • View our selection of featured holiday rentals in Highland Park
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Park while they last

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

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

Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel

Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel

5/5 Excellent
"Great "
A verified traveller stayed at Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel
Posted 22 hours ago
Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel