Holiday rentals in Oak Park

Studio Mins Walk to DT OAK PARK

You will find yourself having a comfortable stay at this centrally located studio just a 5 minute walk from Frank Lloyd Wright Home & Studio, surrounded by beautiful homes yet right next to a variety of shops, cafes and restaurants with Petersen's Ice Cream being right next door, Broken Tart cafe, and Giordano's Pizza right across the street, enjoy the beautiful architecture on a scenic 10 minute walk from this studio to Downtown Oak Park for an even bigger selection of dining and entertainment.

Historic Hotspot: Downtown Oak Park w/parking spot

Short and long-term stays are welcome. Oak Park is known for its historic homes, treelined streets, and downtown area filled with shops and eateries - you’ll appreciate the location. The area is walkable and has easy access to all transportation lines. We include one off-street parking spot. The apartment is great for families and small groups and even set up well for business stays and events. We can provide things such as a changing pad, high-chair, etc. Long-term stays may access laundry.

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

Rockin' 2Bed steps to shops/food/train

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

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Spacious & Stylish Duplex Parking & Walkability

2024 Gut rehab! Spacious w/A+ location! 1 of 2 apts in a two flat. King bed! W/D! This unit = Main floor + finished bsmnt. 3 bdrms + 2.5 baths. Steps to FLW Home. 20 min to downtown Chicago. Walk to dining + train. Open living/dining/kitchen/sunroom. Powder room. Primary w/king + ensuite. 2nd bedroom w/queen + 3rd bedroom w/2 double beds, walk-in closet. 2nd full bath + work/gameroom. Coffee bar, pantry. Private entry/deck. Driveway parking. Upstairs apt not included in this listing.

Guest Favorite Stay in Oak Park| In Unit Laundry

2nd-floor unit with elevator access. Older building with radiant heat managed by the building. Includes an all-in-one electric washer and dryer. Welcome to your stylish Oak Park retreat! This newly remodeled 2BR/2BA apartment blends modern comfort with historic charm. Enjoy a bright space with a full kitchen, cozy living area, and designer touches. Walk to shops, cafes, and parks, or use nearby transit for easy access to Chicago. Perfect for families, friends, or business stays.

Studio Apartment in Oak Park

Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

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.

2-bedroom Apartment in the heart of Oak Park

You and your family will be at the center of Oak Park and a walking distance from architecturally significant homes and the L Train to downtown Chicago. Frank Lloyd Wright's home and studio are a two-minute walk as are shops, dining and entertainment. The apartment features two bedrooms, a large living/dining area and a basement with a foosball and a movie projector.