Oak Park Holiday Rentals

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Holiday Rentals in Oak Park

Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, (18)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (412)
"Great location for museum campus area!!!"
The price is NZ$321
includes taxes & fees
29 May - 30 May
Sentral Michigan Avenue
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Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (85)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is NZ$257
includes taxes & fees
16 Jun - 17 Jun
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"It was a pleasant stay"
The price is NZ$370
includes taxes & fees
5 Jun - 6 Jun
Sonder South Wabash
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (242)
"Clean, friendly, spacious and at an excellent location."
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is NZ$439
includes taxes & fees
29 May - 30 May
Level Chicago – Old Town
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$355
includes taxes & fees
18 Jun - 19 Jun
Found Chicago powered by Sonder
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (63)
" Cozy "
The price is NZ$372
includes taxes & fees
29 May - 30 May
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (103)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is NZ$399
includes taxes & fees
18 Jun - 19 Jun
Sonder Jewelers Row
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is NZ$155
includes taxes & fees
30 May - 31 May
WoodSpring Suites Chicago Addison
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$409
includes taxes & fees
19 Jun - 20 Jun
Sonder The Plymouth
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"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,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"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 NZ$374
includes taxes & fees
2 Jun - 3 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"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!
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
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See all available properties in Oak 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 Oak Park you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6811)
"Very nice well maintained older classic hotel"
The price is NZ$311
includes taxes & fees
29 May - 30 May
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2919)
"Pedro was so helpful from the point of arrival until check out! He was thorough in explaining any questions we had and they were very flexible with late check out as well. I will definitely return in the near future. "
The price is NZ$306
includes taxes & fees
29 May - 30 May
River Hotel
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very good, (1974)
"Very Nice Hotel, In the heart of Chicago. Friendly and professional staff and the vallet guys are top notch not to mention cool. You are legit in walking distance of some if not all of what Chicago has to offer in terms of touristy type tings. "
The price is NZ$344
includes taxes & fees
29 May - 30 May
Eurostars Magnificent Mile
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 Oak 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 Oak 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 Oak Park. Seeing all the best attractions is bound to make you fall in love with Oak 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 Oak Park short-term rentals, that won’t be hard to do.

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.

What are some of the best holiday rentals that Oak Park has to offer?

Your Home Away From Home: This holiday home rental outside of Oak Park offers a fireplace, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

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