Skip to content

Vacation rentals in Oak Park

Find and book unique accommodation on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated holiday rentals in Oak Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Apartment in Oak Park
Sunny Jumbo Studio NO cleaning fee!
Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!
Guest favourite
Loft in Oak Park
Contemporary Oak Park Loft
This affordable loft is ideal for getaways, exploring Chicago, staycations, or work-from-home office space. The loft is a clean, private, second-story apartment with a 5-star rating. The high-speed Wi-Fi and large office area with a roomy, contemporary desk for laptop and ample plugs for all the electronics needed. The kitchenette provides the needed coffee, micro, and mini-fridge with some simple breakfast treats to get you going in the morning. Parking is available on the parking pad.
Superhost
Apartment in Oak Park
Charming Chicago-Style, Vintage, Tv NFL PASS
→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Experience vintage Chicago style living in this richly characteristic brick building, situated in a safe and quiet neighborhood. ★ Property Features: • One block away from the Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable and option to use other apps • Free Laundry Room • Free Parking

Popular amenities for Oak Park holiday rentals

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio184 locals recommend
Downtown Oak Park9 locals recommend
Trader Joe's52 locals recommend
Classic Cinemas Lake Theatre72 locals recommend
Jewel-Osco13 locals recommend
West Suburban Medical Center6 locals recommend

Other great holiday rentals in Oak Park

Guest favourite
Apartment in Oak Park
A Little Slice of Heaven in Oak Park, IL
Guest favourite
Apartment in Berwyn
The Green Bungalow: Charming 1-BR apt. with patio
Guest favourite
Guesthouse in Oak Park
Coachhouse in central OP 4 blk to L
Superhost
Guest suite in Oak Park
Private garden suite in quiet safe Oak Park
Guest favourite
Guesthouse in Oak Park
Stylish Coachhouse in lovely Oak Park!
Guest favourite
Apartment in Oak Park
Charming 1BR/1BA Hideaway in Oak Park, IL
Guest favourite
Home in Oak Park
Clean, Cozy Duplex with Kitchen & Free Parking
Guest favourite
Apartment in Oak Park
2QB Downtown Oak Park, free parking, CTA & Metra
Guest favourite
Apartment in Oak Park
Historic Hotspot Apartment
Guest favourite
Apartment in Oak Park
Cheerful Oak Park Apartment
Guest favourite
Apartment in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
Guest favourite
Guesthouse in Oak Park
Sunny Coach House in Historic Oak Park

Quick stats about holiday rentals in Oak Park

Total rentals

320 properties

Wi-Fi availability

310 properties include access to Wi-Fi

Rentals with dedicated workspaces

170 properties have a dedicated workspace

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

16K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Oak Park