Oak Park Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Oak Park

Chic Suite/Mins to L Train /Laundry/Free Parking
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
Cozy modern unit w/ easy access to downtown Chi
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
Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (426)
"Great experience overall."
The price is HK$1,399
per night
1 Jul - 2 Jul
Sentral Michigan Avenue
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (94)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is HK$689
per night
2 Jul - 3 Jul
Sonder Market Hall
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (309)
"Pretty nice but the outlet and few other items not functioning "
The price is HK$1,533
per night
2 Jul - 3 Jul
Sonder South Wabash
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, (249)
"Parking should be available at a discounted rate. Not free, but in and out privileges at the least would stay agin, if I did not need to travel all over Chicago"
Kasa Magnificent Mile Chicago
Found Chicago powered by Sonder
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (131)
"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 HK$1,331
per night
1 Jul - 2 Jul
Found Chicago powered by Sonder
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (212)
"Loved all the neighborhood dogs & farmers market"
The price is HK$2,219
per night
16 Jun - 17 Jun
Level Chicago – Old Town
Sonder The Burnham
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (77)
"Very close to Kent Law school. "
The price is HK$1,955
per night
14 Jun - 15 Jun
Sonder The Burnham
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (34)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"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!"
The price is HK$2,278
per night
18 Jun - 19 Jun
Kasa River North Chicago
Sonder Jewelers Row
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (107)
"Loved it "
The price is HK$1,745
per night
18 Jun - 19 Jun
Sonder Jewelers Row
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)
"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$703
per night
9 Jun - 10 Jun
WoodSpring Suites Chicago Addison
Kasa South Loop Chicago
Living area
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"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
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is HK$1,535
per night
2 Jul - 3 Jul
Sonder The Plymouth
Luxury Home Away From Your Home
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"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
Walking distance to restaurants, shops and Lake Michigan,
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,
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)
"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$1,390
per night
9 Jun - 10 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)
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
LakeHouse
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (7)
"Great"
LakeHouse
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.

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

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6853)
"Perfect location to museum and restaurants. Good for family and friends "
The price is HK$1,161
per night
16 Jun - 17 Jun
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Lobby
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, (2365)
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay again."
The price is HK$1,646
per night
7 Jul - 8 Jul
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2956)
"Perfect area for walking around chicago even at night. Felt 100 percent safe and the weather mafe for an emalculat trip. "
The price is HK$1,135
per night
7 Jul - 8 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! 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
  • Use the map to find apartments and other holiday homes in the Oak Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oak Park while they last

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.

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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay again."
A verified traveller stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 2 days ago
Embassy Suites by Hilton Chicago Downtown River North