Oak Park vacation rentals

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Top-rated vacation rentals in Oak Park

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

Superhost

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.

$93 per night

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

$53 per night

Superhost

Apartment in Oak Park

Chic Retreat in Historic Victorian House-Free PKG

You will be in the heart of downtown Oak Park, within walking distance to public transportation that takes you directly to downtown Chicago, restaurants, shops, grocery stores and everything Oak Park has to offer. OCCUPANCY LIMIT IS 2 - NO VISITORS ALLOWED Perfect for long term or short term stays. We kindly ask that you read our full listing description and our house rules prior to booking.

$114 per night

Frequently Asked Questions

Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oak Park?
Yes! Work meets play with ease at over 160 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Oak Park?
Oak Park has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in Oak Park have air conditioning?
Absolutely! We offer over 20 condo rentals with air conditioning in Oak Park. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Oak Park?
Experience the best of Oak Park with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Oak Park have wireless internet?
Absolutely! We offer over 20 condo rentals with wireless internet in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Park have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.

Other great vacation rentals in Oak Park

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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!

$106 per night

Superhost

Apartment in Oak Park

50% Monthly Discount for 2024.

This apartment is Perfect for people who plan on using public transportation and enjoy walking. The Green Line CTA "L" train is only 3 blocks away and departs every 10 minutes. You can take the train from either airport, only $3. You can also take a Taxi or Uber from the Airport, around $80. Easy access to Frank Lloyd Wright Home and Studio. Within walking distance are incredible dining experiences, charming shops, and galleries.

$149 per night

Superhost

Apartment in Oak Park

Oak Park Charmer

You'll be staying in the 1st floor of a classic Chicago-style 2 flat. Your apartment (which is completely separate) has hard wood floors throughout, plus a brand new kitchen and bath. Stainless steel appliances and all those essential kitchen tools make this an ideal location for those guests who enjoy eating in, as well as exploring wonderful local eateries. Walk to restaurants, shops and the historic Frank Lloyd Wright homes just a few blocks away. High speed WIFI and parking on premises.

$122 per night

Superhost

Apartment in Forest Park

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

$91 per night

Superhost

Condo in Oak Park

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. This way those that want to go to bed early can do so without ruining the others' fun! The entire space is yours while you are with us. The private deck is shared with our neighbor, but is so large that you will see that you have your own space. I am available anytime. Just text or call me should you need anything! Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. The apartment also boasts access to the metro around the corner, for a quick 20-minute ride into the center of Chicago. We are steps from the green line, which can get you anywhere in the city of Chicago. Private parking is available to you just behind the building. Please only use the space that is designated for 109-unit 2B. Thanks! I keep wine and soft drinks on hand. If you choose to partake, please just leave $20 per bottle, and .50/can. I know how it can be to be somewhere and not want to have to go out and get something when you are thirsty!

$166 per night

Superhost

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.

$168 per night

Superhost

Apartment in Forest Park

Village Cottage - Extended Stay Studio, Pets OK

Welcome to Guest Nest Furnished Stays where you can "Stay Like a Local"! We offer furnished neighborhood lodging in walkable, livable areas in the near-west suburbs of Chicago. We own and manage these small, vintage-boutique apartment buildings and convert some or all of our units to furnished apartments available for extended stays. We specialize in offering fully furnished, stylish, and comfortable neighborhood stays.

$75 per night

Superhost

Apartment in Chicago

Explore Chicago from an Urban Sanctuary with Free Parking

A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.

$59 per night

Superhost

Guest suite in Oak Park

Private garden suite in quiet safe Oak Park

Keep it simple and peaceful while staying in Oak Park. Enjoy this classic garden unit located in an idealistic tree covered neighborhood. Located a 10 min from the Frank Lloyd Wright Home and Studio and Ernest Hemingway home and museum. Green line CTA is a 10 min walk away as well with easy access to Chicago. Enjoy historic Oak Park, thriving Chicago, and a good sleep. Or come to work from home, Netflix, and relax.

$114 per night

Superhost

Condo in Chicago

Urban Comfort in the Heart of Chicago

Proud to be amongst the highest rated listings in the city. This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

$95 per night

Superhost

Guesthouse in Oak Park

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.

$126 per night

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