Oak Park Vacation Rentals

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Make Oak Park your next getaway

Oak Park, IL vacation rentals

Top Oak Park property types

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House rentals

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Apartments

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Popular amenities for Oak Park vacation rentals

Popular
Dog-friendly Internet A/C
Spacious Oak Park Home, 11 Mi to Downtown Chicago!
3 Bedroom | 2 Bath | Sleeps 6

Spacious Oak Park Home, 11 Mi to Downtown Chicago! - Oak Park, IL

$405 avg / night
(excludes fees and taxes)
4.71 (7)
Classic Oak Park Home, 11 Mi to Downtown Chicago!
4 Bedroom | 1.5 Bath | Sleeps 8

Classic Oak Park Home, 11 Mi to Downtown Chicago! - Oak Park, IL

$383 avg / night
(excludes fees and taxes)
4.5 (4)
Oak Park Home w/ Grill - 5 Mi to Garfield Park!
3 Bedroom | 1 Bath | Sleeps 6

Oak Park Home w/ Grill - 5 Mi to Garfield Park! - Oak Park, IL

$311 avg / night
(excludes fees and taxes)
5.0 (4)
Shop, Dine & Unwind: Oak Park Home w/ Private Yard
4 Bedroom | 2 Bath | Sleeps 9

Shop, Dine & Unwind: Oak Park Home w/ Private Yard - Oak Park, IL

$272 avg / night
(excludes fees and taxes)
Pet Friendly: 8 Mi to Chicago - Fenced Backyard!
3 Bedroom | 1 Bath | Sleeps 9

Pet Friendly: 8 Mi to Chicago - Fenced Backyard! - Oak Park, IL

$264 avg / night
(excludes fees and taxes)

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Recent Oak Park guest reviews

My three sisters visited from out of town and we stayed together in the house. The accommodations were perfect for us. The house was spacious, clean, well-furnished and very comfortable. Although located on a fairly busy street, the home was so well insulated that we never heard any street noise, even if a window was open, which made for fine sleeping in the very comfortable beds. Each unit of the two-flat has its own conveniently-located garage in back of the house. Two minor negatives: The small back outdoor space could use some landscaping and the instructions for checking out seem excessive, given that we paid a cleaning fee. We were told to strip all the beds, take out the garbage and recycling, and run the dishwasher and put away the dishes. There was no time left before we were leaving to do that, so we had to leave the dishwasher running. Other than those minor caveats, we were very pleased with our stay there and highly recommend it to others.
Christine . | May 2025
We will absolutely be booking this place Unit again. Our host contact Sylvia was exceptional. The only reason why I am not giving 6/5 stars is because we had issues with the tenants renting the other Unit within the home. We were Unit 1 and there were other renters in Unit 2. Our host was very helpful and efficient at navigating any issues. The home is gorgeous, spacious, clean, and has an alley entrance garage for Unit 1 renters. It is a 3 minute walk from Broken Tart, the BEST bakery in Oak Park and a short drive/uber ride from Chicago. The green line also has an Oak Park stop that can take you to and from the city. In the future, we will book both units with our family to ensure we have the safest and most optimal experience.
Annmarie . | Jan 2025
great place very spacious
Matt . | Aug 2024
Oak Park vacation rental FAQ

Yes. 53 of our Oak Park vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Oak Park vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Oak Park team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Oak Park, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning