Holiday rentals in Oak Park

4.91 out of 5 average rating, 485 reviews

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, fridge, microwave, coffee maker and kettle, it is flexible for individuals or small groups of no more than 4 people. 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.

Superhost

4.84 out of 5 average rating, 103 reviews

Bright & Gorgeous- 5* Location- Queen Beds - Pkg

Leave your worries behind at this peaceful, secure retreat with plenty of space to relax. 2nd-floor duplex to 3rd floor. Just a 15-minute drive to/from downtown. Easily walk to everything: - Groceries, sushi, coffee shop, brewery - Nightlife, live music, and great food - Playgrounds, parks, public pool, & tennis courts Enjoy all the comforts of home in a charming, urban-suburban mix. - Only 1.5 blocks to the Oak Park Av. CTA "L" Blue Line stop & I-290 Housebroken dogs welcome.

4.86 out of 5 average rating, 292 reviews

Cozy and Character-Rich Chicago Style, 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

4.94 out of 5 average rating, 176 reviews

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.

4.9 out of 5 average rating, 304 reviews

Flat in Berwyn

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

4.97 out of 5 average rating, 116 reviews

Home in Oak Park

Garden Unit, King & Queen, Kitchenette & Parking

Our comfy, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 4 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max allowed. Minimum age to book is 25. Visit my profile for additional units

Top guest favourite

4.97 out of 5 average rating, 109 reviews

Cheerful Oak Park Apartment

Welcome to our lovely space, located above a unique piano restoration shop. Spacious and relaxing, with plenty to enjoy staying in, and 5-minutes walking distance to cafes, grocery, bars, restaurants, and more. The apartment is down the street from a Botanic Garden, and there is a nice arts district nearby. Easily accessible to downtown Oak Park and Chicago with nearby public transportation and expressway (downtown Chicago is about 25-35 min. drive, 35-45 min. by train).

4.93 out of 5 average rating, 100 reviews

Townhouse in Oak Park

Downtown Oak Park - Luxury 3 bed 3.5 bath Townhome

Entire townhome located in charming downtown Oak Park. Luxury accommodations. Free Parking. Dog friendly. Highly-walkable area. Attached two-car garage. Chicago's El and Metra train stops a short 2-block walk. Both trains bring you to the heart of downtown with the El extending into many Chicago neighborhoods. Shopping, restaurants, Target, Trader Joe's and Frank Lloyd Wright homes within walking distance. TVs logged into Hulu, Disney +, ESPN, Netflix and HBO Max.

Top guest favourite

4.98 out of 5 average rating, 200 reviews

Modern+Spacious W/King Bed, Walk to Town-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, 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. 4 guests maximum-no visitors allowed

4.94 out of 5 average rating, 241 reviews

Apartment in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Instagram-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

4.88 out of 5 average rating, 289 reviews

Cosmopolitan Nest in Oak Park North Side

Whether visiting Oak Park's historic district or exploring the Windy City for the renowned museums and its nightlife, we welcome you into our home. You are guaranteed a peaceful stay in your own apartment with private entrance on the first floor in our single family home. We are a professional family who maintain a quiet residence. CTA public transportation just steps away.

4.98 out of 5 average rating, 189 reviews

Townhouse in Oak Park

Lovely Central Oak Park TH w/parking & on Green el

Great central Oak Park location, close to everything including dining, Green Line, Metra, and OPRF High School. Enjoy farm fresh produce, eggs, and cheese or pick up some famous Farmers Market Donuts from the Oak Park Farmers Market just steps out your front door every Saturday May-October. Free (driveway) parking for one car. Backyard & deck space off the kitchen.

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Popular amenities for Oak Park holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oak Park

4.85 out of 5 average rating, 34 reviews

Walkable Oasis: Your Chic Loft Awaits (Near Shops)

RobertRating, 5 stars6 days ago

Laura and I were very pleased with our choice to stay at Teretha’s place. We appreciated its location on the third floor in the back of the building away from the street and noise. The neighbors were quiet as well. Although the building was older, it was well kept and had a classic charm. The kitchen and other rooms had everything we needed to feel at home. It was about a seven minute walk through a wonderful neighborhood to many restaurants and stores as well as to the “L” train which takes you directly downtown. We would happily stay here again. It was easy to communicate with Teretha - she was helpful and friendly and responded quickly to our questions.

4.94 out of 5 average rating, 305 reviews

Single bedroom with Asian decor in family home

MichaelRating, 5 stars6 days ago

A very nice house close to the metro and in a peaceful suburb. John and Daniel was very welcoming hosts and gave me helpful hints on places to eat in the local area.

Top guest favourite

4.95 out of 5 average rating, 382 reviews

Antique Filled Home

LaurentRating, 5 stars3 days ago

Tom and Grace were very welcoming. They encouraged us to think of their home as ours. It was lovely, on a lovely street in the relaxing and lovely town of Oak Park. Close to the metro trains. Close to Oak Park downtown. Convenient to downtown Chicago. Loved eating in front porch. Great parking spot. Did not use the car all week. Walking neighborhood. A lovely stay all around.

Apartment in Oak Park

4.74 out of 5 average rating, 105 reviews

Chic Suite/Mins to L Train /Laundry/Free Parking

KailynRating, 5 stars6 days ago

Ali’s place was beautiful and clean! Perfect place to stay for a weekend trip with a good price Wonderful location and cute place. Very responsive and kind host and was super fast to respond to our booking request, would gladly stay again!

4.92 out of 5 average rating, 273 reviews

Hotel room in Rosemont

Relaxing Standard Room l Free Airport Shuttle

AlexeiRating, 5 stars2 weeks ago

easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

Flat in Forest Park

5 out of 5 average rating, 9 reviews

Luxurious Lifestyle

ArielRating, 5 stars4 days ago

Restful, clean, beautiful, and low-stress! Great visit!!

Superhost

4.78 out of 5 average rating, 23 reviews

Finished basement with bedroom

OdessaRating, 5 stars2 weeks ago

Emma was an awesome host, very warm, welcoming, and friendly, and always responded/communicated promptly! As for the room/space, it was clean and cozy and just as described and pictured. I highly recommend and I would definitely love to come back if I’m ever in the area again!