House holiday rentals in Oak Park

Find and book unique houses on Airbnb

Top-rated house rentals in Oak Park

Guests agree: These houses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 160 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top Guest favourite

Home in Berwyn

4.98 out of 5 average rating, 154 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow—the perfect pad for up to 4 friends. Featuring two spacious bedrooms, each with a king bed and luxury linens, a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favourite

Home in North Park

4.95 out of 5 average rating, 175 reviews

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Top Guest favourite

Home in Forest Park

4.98 out of 5 average rating, 121 reviews

NEW Gather in spacious 3 bedroom 2 bath home

CA relief: if IL is an option for temporarary housing, please reach out! I have 4 properties I will do whatever I can. Introducing Mohr Cottage in the heart of Forest Park. Spacious & recently updated 3 bedroom 2 full bath 2 story home is perfect for families or large groups looking space & comfort. Quiet residential neighborhood, blocks from restaurants, shops, coffee. Dogs welcome. Near public transportation, easy access to expressway to downtown Chicago. STRICT Non-smoking property.

Guest favourite

Home in Oak Park

4.97 out of 5 average rating, 129 reviews

Garden Apt, King & Queen, Kitchenette w/ 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 6 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. Booking age 25. Visit my profile for additional units. Booking minimums flexible.

Guest favourite

Home in Forest Park

4.9 out of 5 average rating, 289 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Guest favourite

Home in Logan Square

4.91 out of 5 average rating, 117 reviews

Kid friendly 2 bedroom w/ private office

Come enjoy a hip trip to Logan Square, Chicago! Minutes from local bars, restaurants, parks, the bike trail, and public transit, our toddler friendly, 2 bedroom 1st floor apartment has all you need! Cozy bedrooms and brightly lit common spaces make our space inviting and relaxing. Enjoy a private dedicated work from home space with large windows and tons of light. A front porch swing is also great for a morning cup of coffee or adult beverage wind down. We can't wait to host you!

Guest favourite

Home in Wicker Park

4.97 out of 5 average rating, 252 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite

Home in Portage Park

4.98 out of 5 average rating, 206 reviews

The Evergreen House

Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.

Superhost

Home in Brookfield

4.89 out of 5 average rating, 107 reviews

The Brookfield Breakaway w/ Game Room

This stylish place to stay is perfect for group trips. This split level home has an open concept living room and dining room combo. The gorgeous kitchen has exceptional attention to detail. There are three bedrooms and one bathroom upstairs. Downstairs you’ll find a master suite equipped with its own living space and en suite bathroom. Relax outside on our sectional and enjoy BBQ time with your loved ones. There’s enough space for everyone to enjoy.

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 110 reviews

Beautiful Chicago Greystone

Spacious, private, 4 bedroom condo 15 minutes directly west of the city center. Minutes away from the West Loop, Garfield Conservatory, Downtown, and United Center. Ideal public transportation access with multiple bus stops within 1 block radius, 2 blocks away from Blue Line CTA, 1 mile away from Pink Line CTA. Exquisite back porch and patio with access to grill and patio furniture. Onsite laundry per request Local hosts!

Top Guest favourite

Home in Lombard

4.99 out of 5 average rating, 117 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!