Holiday Rentals in Oak Park

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Holiday Rentals in Oak Park

Apartment in Oak Park

2.0 star property
The price is €372
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Condo in Oak Park

9.6 out of 10, Exceptional, (57)
"The home was very clean, had easy parking, and really convenient to downtown Oak Park where there are many restaurants to choose from. The communication from the host was wonderful and we would definitely stay here again. "
United States
Jill J.
The price is €169
includes taxes & fees
1 Dec - 2 Dec
Chic Suite/Mins to L Train /Laundry/Free Parking

Apartment in Oak Park

8.8 out of 10, Excellent, (24)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is €190
includes taxes & fees
1 Dec - 2 Dec
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Apartment in Oak Park

9.0 out of 10, Wonderful, (4)
"Very responsive, parking and nice layout "
United States
Cynthia B.
The price is €238
includes taxes & fees
30 Nov - 1 Dec
Comfy 2-bedroom apartment with AC, WiFi in Oak Park

Apartment in Oak Park

9.8 out of 10, Exceptional, (69)
"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 €264
includes taxes & fees
1 Dec - 2 Dec
Cozy, Comfortable and Convenient apartment. Close to everything!

Apartment in Oak Park

9.6 out of 10, Exceptional, (96)
"Great spot within a real nice neighborhood. Plenty of places close by to check out. The host Ali is real easy to work with and very friendly. I'll be back for future visits. "
United States
Justin S.
The price is €214
includes taxes & fees
30 Nov - 1 Dec
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Apartment in Oak Park

9.8 out of 10, Exceptional, (17)
"Very impressed with the neighborhood and the cleanliness of the unit! Beds were very comfy too! Thank you for hosting our family and looking forward to returning another time!"
United States
Katie S.
The price is €322
includes taxes & fees
11 Dec - 12 Dec
Spacious, lovely 2bed 1bath with free parking

Apartment in Oak Park

8.2 out of 10, Very good, (31)
"Excellent location, very spacious layout.Lots of items to be able to stay comfortably. Very comfortable beds and pillows very clean towels"
United States
Krista W.
The price is €212
includes taxes & fees
3 Dec - 4 Dec
Oak Park Queen

Holiday Home in Oak Park

10.0 out of 10, Exceptional, (12)
"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 €409
includes taxes & fees
1 Dec - 2 Dec
Vintage Urban Retreat

Apartment in Oak Park

9.0 out of 10, Wonderful, (2)
"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 €513
includes taxes & fees
15 Dec - 16 Dec
Beautiful, cozy stay in Historic Frank Lloyd Wright District

Holiday Home in Oak Park

10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is €438
includes taxes & fees
1 Dec - 2 Dec
Modern Victorian Vibes ❤️ | Character & Charm

Holiday Home in Oak Park

9.8 out of 10, Exceptional, (18)
"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 €598
includes taxes & fees
11 Dec - 12 Dec
Chic 3bed 2bath Home with free parking close to United Center

4BR Corporate Suite Central and Modern

2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is €1,183
includes taxes & fees
30 Nov - 1 Dec
4BR Corporate Suite Central and Modern

Mobile Home in Burr Ridge

10.0 out of 10, Exceptional, (33)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is €162
includes taxes & fees
2 Dec - 3 Dec
Less is more! Pet friendly Tiny Home near Chicago!

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is €127
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is €141
includes taxes & fees
1 Dec - 2 Dec
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is €141
includes taxes & fees
2 Dec - 3 Dec
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is €141
includes taxes & fees
3 Dec - 4 Dec
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is €156
includes taxes & fees
1 Dec - 2 Dec
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is €141
includes taxes & fees
30 Nov - 1 Dec
Stylish 1BR in West Loop
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, 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 €90 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?

LakeHouse: This holiday home rental outside of Oak Park is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Oak Park?

With 28 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.