Oak Park Vacation Rentals

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Vacation Rentals in Oak Park

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 447 reviews
"Great location and the view was fabulous! We had a very comfortable stay. Communication was excellent."
The price is RM 802
per night
2 Jul - 3 Jul
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, 100 reviews
"I love sonder and loved this location! Only downside is that it is virtually impossible to get in touch with anyone on their support side. Hotels.com attempted to help me as much as they could but likely ran into similar issues. They really push communication through their app but since I was having some issues with my Apple ID I wasn’t able to download and use the help which made it impossible for me to get in touch with them. I wanted to stay another night but ended up booking elsewhere...
The price is RM 608
per night
10 Jul - 11 Jul
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 319 reviews
"Comfortable to stay"
The price is RM 746
per night
2 Jul - 3 Jul
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 259 reviews
"The location is great and the room is fully equipped with the useful home appliances like dish washer, laundry and dryer. It’s very helpful for the long stay travelers."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 219 reviews
"I found out that the problem is more me - i am just not a fan of central Chicago - too much traffic-sirens etc., Otherwise the hotel and amenities were fine. "
The price is RM 1,144
per night
30 Jun - 1 Jul
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 135 reviews
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is RM 524
per night
14 Jul - 15 Jul
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 80 reviews
"The stay was straight forward. Login with the passcode and get in. But no one at the reception so some nuances are not easy. For e.g. no early check in even if there are rooms. Also, for long stays, they cant change sheets or towels and no cleaning. It is an interesting concept but not so sure about long term stays like 4-5 days"
The price is RM 1,009
per night
30 Jun - 1 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, 38 reviews
"Property was in a safe, walkable area with plenty of food options. It also wasn't far from downtown Chicago/Michigan Ave. The rooms were nice and clean."
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 191 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 RM 424
per night
20 Jun - 21 Jun
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 70 reviews
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
The price is RM 789
per night
30 Jun - 1 Jul
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, 111 reviews
"We had a wonderful stay in the very comfortable apartment. I chose it for the location near Millenium Park and because it was a one bedroom. The apartment had excellent furnishings and faciilties. We had two difficulties during our stay, with the AC and with the washing machine, and both were solved quickly by the staff. They were responsive and went the extra mile to be sure everything was okay. We were also right over the L train, but with AC running I didn’t even notice it and slept great....
The price is RM 942
per night
7 Jul - 8 Jul
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 166 reviews
"The room was spacious and comfortable, with a great view of the city. Location was perfect for sightseeing in the south loop and buses to museums and elsewhere were a short walk from the building. We parked our car and never used it. Neighborhood felt safe and there was a Target just down the street for supplies. It was nice to have an apartment and kitchen to make relaxing after a day out more comfortable. For what we got it was a great bargain, comparable to the cost of nice hotels but way...
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is RM 665
per night
15 Jul - 16 Jul
Sonder The Plymouth
Sonder The Opal
3.5 star property
8.2 out of 10, Very good, 15 reviews
"I like that was contactless and easy to access. "
The price is RM 977
per night
1 Jul - 2 Jul
Sonder The Opal
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, 29 reviews
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is RM 1,010
per night
2 Jul - 3 Jul
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, 8 reviews
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is RM 546
per night
26 Jun - 27 Jun
Ground Floor Studios in Chicago by 747 Lofts
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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 Oak Park you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 7,006 reviews
"Everything was great except for the breakfast at the restaurant...the waiter appeared to need some training and food off menu was very expensive."
The price is RM 641
per night
1 Jul - 2 Jul
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, 2,399 reviews
"Alma was our checkin agent and she was amazing! So kind!! Do miss the extra sink in bedroom and would love another chair for seating Otherwise great"
The price is RM 858
per night
2 Jul - 3 Jul
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,961 reviews
"Great central location "
The price is RM 637
per night
30 Jun - 1 Jul
River Hotel
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 Oak Park on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Oak Park using one of the methods below:

  • View our selection of featured holiday rentals in Oak Park
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Look no further and take a look at our great range of rental properties in Oak Park!

Frequently asked questions

Are there holiday rentals in Oak Park?

Yes, there are holiday rentals in Oak Park close to Oak Park Conservatory, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

How many holiday rentals are there in Oak Park?

With 23 Expedia holiday rentals, you're guaranteed to find just the right place for your Oak Park stay.

What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Mills Park and Oak Park Conservatory are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Grant Park.

What’s a holiday rental in Oak Park like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Park. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

Recent reviews of Oak Park properties
Expedia verified reviews