Oak Park Holiday Rentals

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Our top choices for Oak Park holiday rentals

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (33 reviews)
"great stay"
United States
matt R.
The price is AU$289
includes taxes & fees
26 Jan - 27 Jan
A quiet stay while you are away
7.6 out of 10, Good, (7 reviews)
"Very responsive, parking and nice layout "
United States
Cynthia B.
The price is AU$408
includes taxes & fees
27 Jan - 28 Jan
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
The price is AU$595
includes taxes & fees
23 Jan - 24 Jan
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
8.8 out of 10, Excellent, (26 reviews)
"Very good communication by the host, well located, clean and comfortable, everything you need!"
Canada
Maxime L.
The price is AU$303
includes taxes & fees
25 Jan - 26 Jan
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
9.8 out of 10, Exceptional, (70 reviews)
"My husband, daughter and I went to Chicago for a weekend getaway and this place was clean, cute and so close to transit. Great place for a small family to stay. "
United States
Amy A.
The price is AU$438
includes taxes & fees
23 Jan - 24 Jan
Cozy, Comfortable and Convenient apartment. Close to everything!
9.6 out of 10, Exceptional, (97 reviews)
"The kitchen was fully equipped and the whole apartment was very comfortable. I especially liked the two very clean bathrooms. There were even curling and flat irons for me to do my hair. Wow! So thoughtful!"
United States
Masooma
The price is AU$392
includes taxes & fees
4 Feb - 5 Feb
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Apartment in Oak Park

Oak Park Queen
8.2 out of 10, Very good, (31 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is AU$337
includes taxes & fees
25 Jan - 26 Jan
Oak Park Queen

Holiday Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14 reviews)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is AU$743
includes taxes & fees
26 Jan - 27 Jan
Vintage Urban Retreat

Holiday Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (28 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is AU$778
includes taxes & fees
25 Jan - 26 Jan
Oak Park Victorian by FLW Studio
9.8 out of 10, Exceptional, (18 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is AU$545
includes taxes & fees
25 Jan - 26 Jan
Spacious, lovely 2bed 1bath with free parking
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AU$450
includes taxes & fees
26 Jan - 27 Jan
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Holiday Home in Oak Park

New! 10-min to Downtown
2.0 star property
The price is AU$929
includes taxes & fees
27 Jan - 28 Jan
New! 10-min to Downtown
9.0 out of 10, Wonderful, (2 reviews)
"This clean, cozy upper level apartment in a duplex was absolutely perfect for our family trip to visit relatives in Oak Park. The neighborhood setting and off-street parking were really convenient, and it was a comfortable (just less than a mile) walk to the downtown area. We will definitely book here for our next trip. "
United States
Kathryn W.
The price is AU$841
includes taxes & fees
27 Jan - 28 Jan
Beautiful, cozy stay in Historic Frank Lloyd Wright District
2.0 star property
The price is AU$977
includes taxes & fees
27 Jan - 28 Jan
Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
9.8 out of 10, Exceptional, (18 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is AU$1,008
includes taxes & fees
25 Jan - 26 Jan
Chic 3bed 2bath Home with free parking close to United Center
9.8 out of 10, Exceptional, (37 reviews)
"We loved it! We were in for a short time and it was perfect!!"
United States
nicole l.
The price is AU$314
includes taxes & fees
27 Jan - 28 Jan
Less is more! Pet friendly Tiny Home near Chicago!

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,059 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is AU$235
includes taxes & fees
26 Jan - 27 Jan
Sentral Michigan Avenue

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$253
includes taxes & fees
27 Jan - 28 Jan
1BR Modern Luxe Apt with In-Unit Laundry

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (414 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
Level Chicago – Old Town

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AU$253
includes taxes & fees
26 Jan - 27 Jan
West Loop Living – Bright 1BR
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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Top Oak Park Hotel Reviews

Find out more about Oak Park

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, 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 favourite 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 depend 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 AU$235 per night. Entering your travel dates in the search wizard might find you 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Oak Park offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Oak Park?

With 30 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 Pleasant Home, 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 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.