Search Holiday Rentals in Oak Park

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Top Holiday Rentals in Oak Park

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The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (23)
"Beautiful, clean, new suites! Highly recommend! Easy to get to from public transport. The pull out sofa bed is not comfortable for those hoping to use it. But the main area bed was a dream! "
The price is £188
per night
6 May - 7 May
The Neighborhood Hotel-Little Italy
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (6)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is £138
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Fridge, microwave, oven, stovetop
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (11)
"The place was extremely simple and easy. The check in was really easy, the place was very affordable, the place was extremely clean, the house owner was really easy to get a hold of and fast with answering questions. Overall a great experience!"
The price is £358
per night
9 May - 10 May
Game room/King Bed /Wi-Fi/Deck + Fire Pit
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Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (17)
"Great apartment! Perfect for 2 adults and 2 teens. Extremely close to Blue Line into Chicago. Easy drive to Wheaton (could have easily taken the Metra instead). Recommend Cuzzo pizza and Addis Cafe in Oak Park. One of us came down with a cold- grocery and drugstore nearby, and we spent the day playing cards and watching movies. Kitchenette was great for making our own (read: cheap) breakfasts each day. Thank you!"
Cozy modern unit w/ easy access to downtown Chi
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (15)
"My wife and I spent a long weekend here. The apartment had plenty of room, was nicely decorated. The kitchen contained everything we needed to cook a full meal (which we did not). The bed is very comfortable. Ride service to downtown averaged $25. It was perfect."
The price is £153
per night
3 May - 4 May
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is £282
per night
5 May - 6 May
national historic home near downtown airports no parties no events
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (388)
"We really enjoyed our stay at Sentral. The property is conveniently located near Art Institute of Chicago, Millennium and Grant Park."
The price is £166
per night
28 May - 29 May
Sentral Michigan Avenue
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | 42-inch Smart TV with digital channels, TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (160)
"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
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (46)
"Only real issue was no late night (after 9) dining options. I got in later than expected & couldn't find even a fast food joint open after 9. Settled for 7-11 Pizza. "
The price is £182
per night
5 May - 6 May
Sonder The Burnham
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (7)
"Great little home away from home. Definitely need to be painted and maintenance upgrades need to be addressed but other than that we had a great time"
The price is £145
per night
9 May - 10 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (294)
"Overall the stay was amazing. We will definitely be booking here again."
The price is £164
per night
28 May - 29 May
Sonder South Wabash
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (206)
"Nice"
The price is £204
per night
12 May - 13 May
Level Chicago – Old Town
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (28)
"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 £271
per night
29 May - 30 May
Sonder Greektown
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (65)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is £222
per night
22 May - 23 May
Sonder The Plymouth
Bar (on property)
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (97)
"The only real problem is train noise I was lucky that my unit was at the end of hallway so relatively far from train noise but they moved us for one night to another unit because of plumbing issue and as extremely noisy "
The price is £166
per night
28 May - 29 May
Sonder Jewelers Row
Superior Studio, City View | Individually decorated, individually furnished, desk
Sonder Market Hall
3.5 star property
8.0 out of 10, Very good, (74)
"The property was nice, clean and fresh. The Studio was really nice and updated. "
The price is £109
per night
5 May - 6 May
Sonder Market Hall
Full-sized fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is £184
per night
28 May - 29 May
Sonder The Opal
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (123)
"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 £192
per night
29 May - 30 May
Found Chicago powered by Sonder
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (183)
"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 £61
per night
7 May - 8 May
WoodSpring Suites Chicago Addison
Don't see what you're looking for?
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.

Oak Park Holiday Rental Travel Info

Number of holiday rentals
9
Popular accommodation
Oak Park apartments
Known landmarks
Art Institute of Chicago, Chicago Riverwalk and Chicago Theatre
International airports
Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

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

View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2840)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."
The price is £150
per night
12 May - 13 May
River Hotel
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very good, (1881)
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The price is £159
per night
12 May - 13 May
Eurostars Magnificent Mile
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2545)
"Its was a nice stay. "
The price is £143
per night
15 May - 16 May
Warwick Allerton - Chicago
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.

Everything you need to know about Oak Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Park holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Park holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Park. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Park holiday rentals we have selected for you start as low as £61 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Park holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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