Oak Park Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Oak Park holiday rentals

2 bedrooms

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$995
HK$2,008 total
includes taxes & fees
2 Mar - 3 Mar
The Oak Park Loft
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is HK$560
HK$1,635 total
includes taxes & fees
4 Mar - 5 Mar
A quiet stay while you are away
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is HK$1,014
HK$2,217 total
includes taxes & fees
2 Mar - 3 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very good, (32 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is HK$697
HK$1,765 total
includes taxes & fees
1 Mar - 2 Mar
Oak Park Queen
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"Great location in a quiet neighborhood! Beautiful Victorian house that was perfect for our company. Every amenities you could ask for and washer/dryer was excellent for our international co founders and they were very impressed with dry time. We will be staying here every time we are in Chicago. "
United States
Mike B.
The price is HK$1,162
HK$3,721 total
includes taxes & fees
2 Mar - 3 Mar
Vintage Urban Retreat
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is HK$1,338
HK$3,949 total
includes taxes & fees
2 Mar - 3 Mar
Oak Park Victorian by FLW Studio
Interior

Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking
Oak Park
9.6 out of 10, Exceptional, (19 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is HK$1,232
HK$2,852 total
includes taxes & fees
27 Feb - 28 Feb
Spacious, lovely 2bed 1bath with free parking
Dining

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
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 HK$1,258
HK$2,380 total
includes taxes & fees
2 Mar - 3 Mar
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Glad to have found this gem in Oak Park for a two-night stay with friends. Booking and checking in was easy and seamless. Free street parking was a huge bonus. The space was super cute and comfortable. We enjoyed walking around the neighborhood and getting into the city was super easy (we chose to use Lyft instead of the train, but there are train stations within walking distance. Would definitely book this property again the next time I come to Chicago."
United States
Emily B.
The price is HK$845
HK$2,302 total
includes taxes & fees
27 Feb - 28 Feb
Cozy, Comfortable and Convenient apartment. Close to everything!
TV, DVD player, books, video library

First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is HK$1,198
HK$2,527 total
includes taxes & fees
1 Mar - 2 Mar
First floor of Historic Oak Park Villa, Grge:2Cars
Interior

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
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 HK$1,760
HK$5,302 total
includes taxes & fees
27 Feb - 28 Feb
Chic 3bed 2bath Home with free parking close to United Center
Smart TV, books

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (58 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is HK$528
HK$1,545 total
includes taxes & fees
8 Mar - 9 Mar
Chic Suite/Mins to L Train /Laundry/Free Parking
Exterior detail

Top floor of Historic Oak Park Villa /Grge: 2Cars

Top floor of Historic Oak Park Villa /Grge: 2Cars
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The property was beautiful, spacious, warm, and very charming!"
United States
Sarah S.
The price is HK$1,291
HK$2,579 total
includes taxes & fees
2 Mar - 3 Mar
Top floor of Historic Oak Park Villa /Grge: 2Cars
TV, table football

New! 10-min to Downtown

New! 10-min to Downtown
Oak Park
The price is HK$2,206
HK$5,035 total
includes taxes & fees
1 Mar - 2 Mar
New! 10-min to Downtown
TV

Top floor of Historic Oak Park Home /2 Car Garage

Top floor of Historic Oak Park Home /2 Car Garage
Oak Park
9.6 out of 10, Exceptional, (23 reviews)
"Our stay was wonderful. The location with parking was perfect."
United States
Joan W.
The price is HK$1,152
HK$2,407 total
includes taxes & fees
2 Mar - 3 Mar
Top floor of Historic Oak Park Home /2 Car Garage
Interior

Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago

Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
Oak Park
10.0 out of 10, Exceptional, (1 review)
"Great"
United States
Ayden R.
The price is HK$2,542
HK$5,448 total
includes taxes & fees
1 Mar - 2 Mar
Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
Terrace/patio

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Oak Park
8.8 out of 10, Excellent, (29 reviews)
"Very good communication by the host, well located, clean and comfortable, everything you need!"
Canada
Maxime L.
The price is HK$563
HK$1,657 total
includes taxes & fees
3 Mar - 4 Mar
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Interior

Beautiful, cozy stay in Historic Frank Lloyd Wright District

Beautiful, cozy stay in Historic Frank Lloyd Wright District
Oak Park
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.
Beautiful, cozy stay in Historic Frank Lloyd Wright District
Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is HK$1,198
HK$2,241 total
includes taxes & fees
1 Mar - 2 Mar
Historic Oak Park Home
Dining

The Oak Park Loft, Including Garage

The Oak Park Loft, Including Garage
Oak Park
10.0 out of 10, Exceptional, (10 reviews)
"Private, historic, well, equipped, comfortable, and the owners were very friendly and accessible."
United States
James
The Oak Park Loft, Including Garage
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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Very nice. Hotel lobby has the best drinks. Nice place for couples. Room is cute"
Victor 2-night trip
Posted 21 hours ago
Aloft Chicago Mag Mile

Find out more about Oak Park

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:

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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?

A Home Away From Home!: This holiday home rental outside of Oak Park offers a fireplace, a garden 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 Madison Street Theatre, whereas Oak Park Conservatory and Euclid Square 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.