Search Holiday Rentals in Oak Park

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Top Holiday Rentals in Oak Park

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (586)
"Great stay. Will stay again!"
The price is ฿4,057
฿5,788 total
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (203)
"Overall, we really enjoyed our stay! The area was lovely and quiet, so nice to sit at the park right beside! I was worried about the noise when it came to sleeping, but I was able to sleep soundly (i did have noise cancelling headphones on though). The bed was super comyfy! The walls are thin though, we could hear conversations and music. This place was very accommodating! They have everything as stated in their listing. The kitchenette is so great! Staff was very friendly whenever I had...
The price is ฿2,398
฿2,815 total
includes taxes & fees
10 Dec - 11 Dec
Sonder Market Hall
Sonder South Wabash
36-inch flat-screen TV with digital channels, TV
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (389)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is ฿4,463
฿5,239 total
includes taxes & fees
11 Dec - 12 Dec
Sonder South Wabash
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
3.5 star property
9.6 out of 10, Exceptional, (96)
"Very safe . Clean and spacious "
The Neighborhood Hotel-Little Italy
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (329)
"Kasa was a nice place to stay while visiting Chicago for a weekend. It was clean and close to transportation and other attractions. However, a downside is that there are no black out curtains/shades in the apartment so it is very bright in the morning. Otherwise it was a good stay. "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (268)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is ฿6,134
฿7,794 total
includes taxes & fees
15 Dec - 16 Dec
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (175)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is ฿4,336
฿5,091 total
includes taxes & fees
10 Dec - 11 Dec
Found Chicago powered by Sonder
Sonder The Burnham
Marina
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (113)
"Very convenient location, the apartment was impeccable "
The price is ฿4,998
฿5,867 total
includes taxes & fees
22 Nov - 23 Nov
Sonder The Burnham
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (231)
"The facilities areexcellent and has a front reception desk constantly manned fir security. The personnek were very polite, efficient, and attentive. Very professional and enhanced the sense of security and service. Emails detailing check in and check out were excellent. The embedded photos in those emails also were very helpful and made everything so very easy! Will be using Kasa again in future visits!"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (131)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is ฿3,945
฿4,630 total
includes taxes & fees
11 Dec - 12 Dec
Sonder Jewelers Row
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (99)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is ฿4,751
฿5,578 total
includes taxes & fees
19 Nov - 20 Nov
Kasa River North Chicago
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.2 out of 10, Very good, (82)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is ฿5,596
฿6,569 total
includes taxes & fees
15 Dec - 16 Dec
Sonder The Plymouth
Sonder The Opal
Exterior
Sonder The Opal
3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is ฿5,036
฿5,911 total
includes taxes & fees
10 Dec - 11 Dec
Sonder The Opal
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (11)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is ฿4,082
฿7,057 total
includes taxes & fees
15 Nov - 16 Nov
Ground Floor Studios in Chicago by 747 Lofts
Sonder Greektown
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is ฿5,344
฿6,274 total
includes taxes & fees
12 Dec - 13 Dec
Sonder Greektown
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 Oak Park you may be interested in

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (8072)
"Thoroughly enjoyed my stay"
The price is ฿2,986
฿3,505 total
includes taxes & fees
25 Nov - 26 Nov
Congress Plaza Hotel
River Hotel
View from property
River Hotel
4.0 star property
8.6 out of 10, Excellent, (3539)
"It was great"
The price is ฿3,785
฿4,443 total
includes taxes & fees
8 Dec - 9 Dec
River Hotel
Embassy Suites by Hilton Chicago Downtown River North
Lobby
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.2 out of 10, Very good, (3193)
"Our family loved the breakfast buffet, reception every evening, and the pool. "
The price is ฿4,129
฿4,847 total
includes taxes & fees
8 Dec - 9 Dec
Embassy Suites by Hilton Chicago Downtown River North
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.

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 26 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 Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Michigan Avenue.

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.