Oak Park Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Oak Park holiday rentals

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)
"great stay"
United States
matt R.
The price is HK$596
HK$1,667 total
includes taxes & fees
3 Mar - 4 Mar
A quiet stay while you are away
Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is HK$994
HK$2,005 total
includes taxes & fees
9 Feb - 10 Feb
At Home in Oak Park
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, (71 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 HK$844
HK$2,299 total
includes taxes & fees
9 Feb - 10 Feb
Cozy, Comfortable and Convenient apartment. Close to everything!
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)
"Super convenient if you want to see the Frank Lloyd wright house - walked to studio and train and great cafes. Perfect location "
United States
Travis S.
The price is HK$625
HK$1,682 total
includes taxes & fees
28 Feb - 1 Mar
Chic Suite/Mins to L Train /Laundry/Free Parking
Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is HK$938
HK$1,941 total
includes taxes & fees
9 Feb - 10 Feb
Historic Oak Park Home
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, (28 reviews)
"Very good communication by the host, well located, clean and comfortable, everything you need!"
Canada
Maxime L.
The price is HK$563
HK$1,628 total
includes taxes & fees
9 Feb - 10 Feb
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
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)
"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 HK$949
HK$2,133 total
includes taxes & fees
10 Feb - 11 Feb
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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$1,284
HK$3,876 total
includes taxes & fees
9 Feb - 10 Feb
Oak Park Victorian by FLW Studio
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
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 HK$1,090
HK$3,627 total
includes taxes & fees
10 Feb - 11 Feb
Vintage Urban Retreat
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$1,094
HK$2,174 total
includes taxes & fees
10 Feb - 11 Feb
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Interior

Oak Park Queen

Oak Park Queen
Oak Park
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 HK$696
HK$1,736 total
includes taxes & fees
11 Feb - 12 Feb
Oak Park Queen
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$873
HK$1,867 total
includes taxes & fees
9 Feb - 10 Feb
The Oak Park Loft
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$731
HK$2,206 total
includes taxes & fees
9 Feb - 10 Feb
Spacious, lovely 2bed 1bath with free parking
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
TV, table football

New! 10-min to Downtown

New! 10-min to Downtown
Oak Park
New! 10-min to Downtown
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$1,758
HK$5,331 total
includes taxes & fees
16 Feb - 17 Feb
Chic 3bed 2bath Home with free parking close to United Center
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.
First floor of Historic Oak Park Villa, Grge:2Cars
Interior

Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago

Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
Oak Park
The price is HK$2,539
HK$7,228 total
includes taxes & fees
9 Feb - 10 Feb
Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
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 price is HK$899
HK$2,073 total
includes taxes & fees
9 Feb - 10 Feb
The Oak Park Loft, Including Garage
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$938
HK$2,132 total
includes taxes & fees
10 Feb - 11 Feb
Top floor of Historic Oak Park Villa /Grge: 2Cars
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Room was clean and looked exactly like the pictures online. Staff were very nice throughout the stay."
Sheri Lynn 2-night trip
Posted 4 hours ago
Eurostars Magnificent 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 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.