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
Flat in Oak Park
Long stays welcome@warm&cute vintage 2BR
This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving
7–14 JulIndividual Host,
£100 per night
4.85 out of 5 average rating, 508 reviews
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.
23–30 AprIndividual Host,
£91 per night
4.98 out of 5 average rating, 339 reviews
Guest favourite
Flat in Oak Park
Bright & Spacious Victorian-FREE PKG walk to train
This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking. *** OCCUPANCY LIMIT IS 4 - NO VISITORS ALLOWED
5–12 DecIndividual Host,
£155 per night
4.98 out of 5 average rating, 264 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
Large sunny 3BR apt. in downtown Oak Park
27 Oct – 3 NovIndividual Host,
£188 per night
4.91 out of 5 average rating, 165 reviews
Guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
4–11 JunIndividual Host,
£112 per night
4.89 out of 5 average rating, 391 reviews
Guest favourite
Flat in Oak Park
Walking Distance to Everything.
17–24 DecIndividual Host,
£171 per night
4.92 out of 5 average rating, 132 reviews
Guest favourite
Flat in Oak Park
A quiet stay while you are away
30 Mar – 6 AprIndividual Host,
£105 per night
4.95 out of 5 average rating, 149 reviews
Guest favourite
Guest house in Oak Park
Coachhouse in central OP 4 blk to L
20–27 AugIndividual Host,
£147 per night
4.88 out of 5 average rating, 451 reviews
Guest favourite
Flat in Oak Park
Cozy Vintage Chicago-Style, 1 bed with Cable
27 Mar – 3 AprProfessional Host,
£74 per night
4.88 out of 5 average rating, 278 reviews
Guest favourite
Flat in Oak Park
A Little Slice of Heaven in Oak Park, IL
2–9 NovIndividual Host,
£98 per night
4.87 out of 5 average rating, 124 reviews
Guest favourite
Flat in Forest Park
Walk to Oak Park from this Newly Remodeled Gem
6–13 JunProfessional Host,
£141 per night
4.99 out of 5 average rating, 179 reviews
Guest favourite
Flat in Oak Park
Lovely 2-bedroom rental in the heart of Oak Park
14–21 FebProfessional Host,
£111 per night
4.98 out of 5 average rating, 80 reviews
Guest favourite
Guest house in Oak Park
Stylish Coachhouse in lovely Oak Park!
8–15 SeptIndividual Host,
£120 per night
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Oak Park
Clean, Cozy Duplex with Kitchen & Free Parking
8–15 AprIndividual Host,
£90 per night
4.96 out of 5 average rating, 54 reviews
Guest favourite
Flat in Oak Park
Cheerful Oak Park Apartment
8–15 MayIndividual Host,
£123 per night
5.0 out of 5 average rating, 60 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