Oak Park Vacation Rentals

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Check prices for these dates

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

Our top choices for Oak Park vacation rentals

Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥19,659
￥39,835 total
includes taxes & fees
Mar 3 - Mar 4
The Oak Park Loft
Exterior

Vacation Home in Oak Park

A quiet stay while you are away
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 ￥10,719
￥32,280 total
includes taxes & fees
Mar 3 - Mar 4
A quiet stay while you are away
Interior

Vacation Home in Oak Park

Chic 3bed 2bath Home with free parking close to United Center
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 ￥35,111
￥106,476 total
includes taxes & fees
Mar 3 - Mar 4
Chic 3bed 2bath Home with free parking close to United Center
Exterior detail

Vacation Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ￥21,067
￥72,175 total
includes taxes & fees
Mar 3 - Mar 4
Oak Park Victorian by FLW Studio
Interior

Apartment in Oak Park

Beautiful, cozy stay in Historic Frank Lloyd Wright District
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 ￥24,578
￥87,806 total
includes taxes & fees
Mar 3 - Mar 4
Beautiful, cozy stay in Historic Frank Lloyd Wright District
TV, DVD player, books, video library

Apartment in Oak Park

First floor of Historic Oak Park Villa, Grge:2Cars
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is ￥23,665
￥50,142 total
includes taxes & fees
Mar 4 - Mar 5
First floor of Historic Oak Park Villa, Grge:2Cars
Interior

Apartment in Oak Park

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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 ￥20,224
￥44,590 total
includes taxes & fees
Mar 3 - Mar 4
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Interior

Vacation Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14 reviews)
"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."
United States
Beryl I.
The price is ￥21,629
￥72,280 total
includes taxes & fees
Mar 3 - Mar 4
Vintage Urban Retreat
TV, foosball

Vacation Home in Oak Park

New! 10-min to Downtown
The price is ￥54,618
￥113,929 total
includes taxes & fees
Mar 3 - Mar 4
New! 10-min to Downtown
TV

Apartment in Oak Park

Top floor of Historic Oak Park Home /2 Car Garage
9.6 out of 10, Exceptional, (23 reviews)
"Our stay was wonderful. The location with parking was perfect."
United States
Joan W.
Top floor of Historic Oak Park Home /2 Car Garage
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Apartment in Oak Park

Historic Oak Park Home
2.0 star property
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 ￥23,665
￥44,421 total
includes taxes & fees
Mar 3 - Mar 4
Historic Oak Park Home
Interior

Apartment in Oak Park

Spacious, lovely 2bed 1bath with free parking
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place and neighborhood."
United States
Charles R.
The price is ￥24,578
￥57,436 total
includes taxes & fees
Mar 3 - Mar 4
Spacious, lovely 2bed 1bath with free parking
Fridge, microwave, oven, stovetop

Apartment in Oak Park

Cozy, Comfortable and Convenient apartment. Close to everything!
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is ￥16,853
￥46,446 total
includes taxes & fees
Mar 3 - Mar 4
Cozy, Comfortable and Convenient apartment. Close to everything!
Interior

Apartment in Oak Park

Oak Park Queen
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 ￥13,904
￥35,032 total
includes taxes & fees
Mar 3 - Mar 4
Oak Park Queen
Dining

Vacation Home in Oak Park

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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 ￥28,089
￥51,272 total
includes taxes & fees
Mar 9 - Mar 10
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Interior

Vacation Home in Oak Park

Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great"
United States
Ayden R.
The price is ￥54,618
￥113,394 total
includes taxes & fees
Mar 4 - Mar 5
Elevated Gem | Sleeps 12 | 20 mins to Downtown Chicago
Exterior detail

Apartment in Oak Park

Top floor of Historic Oak Park Villa /Grge: 2Cars
10.0 out of 10, Exceptional, (5 reviews)
"The property was beautiful, spacious, warm, and very charming!"
United States
Sarah S.
The price is ￥26,001
￥53,002 total
includes taxes & fees
Mar 3 - Mar 4
Top floor of Historic Oak Park Villa /Grge: 2Cars
Terrace/patio

Apartment in Oak Park

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
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 ￥11,236
￥33,052 total
includes taxes & fees
Mar 3 - Mar 4
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Apartment, Private Bathroom | Lounge

Apartment in Oak Park

At Home in Oak Park
3.5 star property
9.4 out of 10, Exceptional, (9 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ￥22,754
￥43,378 total
includes taxes & fees
Mar 3 - Mar 4
At Home in Oak Park
Smart TV, books

Condo in Oak Park

Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (58 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is ￥10,533
￥30,818 total
includes taxes & fees
Mar 8 - Mar 9
Chic Suite/Mins to L Train /Laundry/Free Parking
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"The staff was wonderful and the rooms were clean."
Robert 1-night trip
Posted 7 hours ago
Hilton Chicago

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:

  • View our selection of featured holiday rentals in Oak Park
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  • 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 vacation rentals in Oak Park?

Yes, we have vacation rentals in Oak Park close to Oak Park Conservatory, or you can choose a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Oak Park has to offer?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This vacation home rental outside of Oak Park is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Oak Park?

With 31 Expedia vacation rentals, you're sure 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 vacation rental in Oak Park like?

Vacation rentals are private properties you can stay in for several days or longer in Oak Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.