Holiday rentals in Oak Park

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Top-rated holiday rentals in Oak Park

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

Guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
You have the use of the entire upstairs (with a separate, lockable private entrance) and bicycles. With two bedrooms, bathroom and a common area with a futon, table, fridge, microwave, coffee maker and kettle, it is flexible for individuals, couples, families or small groups. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.
10–17 MayIndividual Host,
€ 123 per night
4.89 out of 5 average rating, 395 reviews
Superhost
Flat 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!
20–27 JanIndividual Host,
€ 159 per night
4.84 out of 5 average rating, 481 reviews
Guest favourite
Flat in Oak Park
Stunning 2bd 1bath w/free parking, W/D & fireplace
Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.
30 Aug – 6 SepIndividual Host,
€ 149 per night
4.88 out of 5 average rating, 103 reviews

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
West Suburban Medical Center6 locals recommend
Jewel-Osco13 locals recommend

Other great holiday rentals in Oak Park

Guest favourite
Flat in Oak Park
Cheerful Oak Park Apartment
21–28 AugIndividual Host,
€ 143 per night
5.0 out of 5 average rating, 62 reviews
Guest favourite
Flat in Oak Park
Lovely 2-bedroom rental in the heart of Oak Park
17–24 FebProfessional Host,
€ 137 per night
4.98 out of 5 average rating, 82 reviews
Guest favourite
Flat in Forest Park
Beautiful Remodel Prime Location
5–12 JanProfessional Host,
€ 96 per night
4.95 out of 5 average rating, 22 reviews
Guest favourite
Flat in Oak Park
Historic Hotspot Apartment
2–9 AprIndividual Host,
€ 138 per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
27 Jun – 4 JulIndividual Host,
€ 124 per night
4.99 out of 5 average rating, 84 reviews
Guest favourite
Guest house in Oak Park
O'Malley Oasis!
31 Aug – 7 SepIndividual Host,
€ 171 per night
4.94 out of 5 average rating, 71 reviews
Guest favourite
Guest house in Oak Park
Stylish Coachhouse in lovely Oak Park!
2–9 AugIndividual Host,
€ 179 per night
4.99 out of 5 average rating, 68 reviews
Guest favourite
Flat in Oak Park
2BR/2BA Oak Park Gem - Ideal Comfort
25 Nov – 2 DecIndividual Host,
€ 182 per night
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Oak Park
Clean, Cozy Duplex with Kitchen & Free Parking
27 Apr – 4 MayIndividual Host,
€ 137 per night
4.97 out of 5 average rating, 59 reviews
Guest favourite
Home in Oak Park
Modern Victorian Charm | Best Location in OP
30 Oct – 6 NovIndividual Host,
€ 431 per night
4.96 out of 5 average rating, 54 reviews
Superhost
Flat in Oak Park
Cozy Modern Oak Park Apartment
22–29 MarIndividual Host,
€ 186 per night
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Oak Park
The Artist's Loft - Oak Park
24 Nov – 1 DecIndividual Host,
€ 192 per night
4.94 out of 5 average rating, 17 reviews

Quick stats about holiday rentals in Oak Park

Total rentals

320 properties

Wifi availability

310 properties include access to wifi

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