Vacation Rentals in Oak Park, IL

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Oak Park, IL holiday rentals
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451 Holiday rentals and Airbnb in Oak Park, IL

Uncover Top-Tier Family Holiday Rentals in Oak Park, IL, United States

Give everyone their own room to relax after a long day of sightseeing at spacious family holiday rentals in Oak Park, IL, United States.

5 Bedrooms 2 Full Bathrooms 1 Parking Space - Oak Park, IL
9.6 47 reviews

5 Bedrooms 2 Full Bathrooms 1 Parking Space

apartment, Oak Park
This five-bedroom Oak Park apartment, ideal for families, is conveniently located near the Blue and Green Lines, offering easy access to Chicago.
The two-level property features a unique layout spanning the first floor and basement, accommodating six guests with amenities including a fully equipped kitchen, two bathrooms, a shared backyard with a gas grill, Netflix, Hulu and Peacock streaming services, and one designated parking space.
Charming And Convenient 3br 1ba Apt - Fully Furnished And Equipped - Fast Internet - Oak Park, IL
8.8 11 reviews

Charming And Convenient 3br 1ba Apt - Fully Furnished And Equipped - Fast Internet

apartment, Forest Park
This Forest Park apartment, situated approximately 13-16km from central Chicago attractions such as Union Station and the Willis Tower, offers convenient access to Midway International Airport (13km).
The 102-square-metre property comprises three bedrooms, one bathroom, and sleeps up to 13 guests, featuring a fully equipped kitchen, in-unit laundry, and free Wi-Fi; private parking is also provided.
Elevated Gem - Sleeps 12 - 20 Mins To Downtown Chicago - Oak Park, IL
10 3 reviews

Elevated Gem - Sleeps 12 - 20 Mins To Downtown Chicago

apartment, Oak Park
This five-bedroom, three-bathroom flat in Oak Park offers proximity to the Frank Lloyd Wright Historic District (644 metres drive) and Ernest Hemingway's House and Museum (966 metres drive), with the Oak Park Metro Station a 13-minute walk away for convenient travel.
This pet-friendly accommodation for up to 12 guests includes air conditioning, Wi-Fi, a fully equipped kitchen with an oven and microwave, and on-site foosball, with covered parking provided for ease of access.
Cozychic 3br Near Chicago| Walk To Train W/parking - Oak Park, IL
9.8 65 reviews

Cozychic 3br Near Chicago| Walk To Train W/parking

apartment, Forest Park
This three-bedroom Forest Park apartment, sleeping seven, offers excellent cleanliness and location ratings, though its precise location within Forest Park requires further clarification regarding proximity to specific attractions.
The family-friendly dwelling includes a kitchen with fridge, freezer, and microwave, air conditioning, parking, and internet access; further details on amenities and interior design are unavailable.

Best Oak Park, IL holiday rentals with parking

2-br Central Oak Park Flat+near Flw Homes+near Trains To Chicago+pets Ok+parking - Oak Park, IL
10 10 reviews

2-br Central Oak Park Flat+near Flw Homes+near Trains To Chicago+pets Ok+parking

apartment, Oak Park
This full-floor flat offers a private retreat in Oak Park, situated two blocks from Frank Lloyd Wright's Unity Temple and a short walk to his Home and Studio, with downtown Oak Park's amenities also within 500 meters.
This three-bedroom residence, accommodating up to five guests, features a newly renovated bathroom, a private front porch deck, a fenced backyard with a fire table, and off-street parking, with internet, air conditioning, and pets welcome.
Architect-designed 5br Oak Park Flat - Oak Park, IL
No reviews

Architect-designed 5br Oak Park Flat

apartment, Oak Park
This five-bedroom, three-bathroom flat in Oak Park is a short walk from historic Oak Park cultural attractions and provides easy access to Chicago's Green Line public transportation.
This recently renovated multi-unit space for ten guests features air conditioning, a garden, a private roof deck, and a fully equipped galley kitchen.
2nd Floor Walk Up Above House. 3 Bed 1 Bath - Oak Park, IL
10 14 reviews

2nd Floor Walk Up Above House. 3 Bed 1 Bath

apartment, Oak Park
This three-bedroom, one-bathroom apartment in Oak Park offers a peaceful, second-floor setting above the main house, its central location requiring further clarification regarding proximity to specific landmarks such as Frank Lloyd Wright's homes and the Oak Park Arts District.
The self-contained flat sleeps three guests and includes a kitchen equipped with a fridge, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews; further details on the exact distances to local attractions and public transport are needed.
Lovely Central Oak Park Th W/parking & On Green El - Oak Park, IL
10 244 reviews

Lovely Central Oak Park Th W/parking & On Green El

house, Oak Park
This charming house is located in a central Oak Park neighbourhood, just a short walk from the Green Line, Metra, and the Oak Park Farmers Market. It has received excellent ratings for location, cleanliness and user experience.
The property has two bedrooms and two bathrooms, making it ideal for families or groups of up to five people. It comes equipped with a kitchen, a garden, parking, and laundry facilities, as well as air conditioning and internet access.

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Discover Holiday Rentals with a Balcony in Oak Park, IL, United States

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Oak Park, IL, United States.

Flexhome Ukrainian Village  2br  Walkable + Private Balcony · Sleeps 6 - Oak Park, IL
8.8 14 reviews

Flexhome Ukrainian Village 2br Walkable + Private Balcony · Sleeps 6

apartment, Chicago
This West Town apartment in Chicago offers convenient access to numerous parks, restaurants, and bars, with major attractions within easy reach.
The 55-square-metre (592-square-foot) flat features two queen-size beds, a sofa, one bathroom, in-unit laundry, and sleeps up to five guests, boasting a dedicated workspace and a smart TV with AirPlay.
Spacious Oak Park Home, 11 Mi To Downtown Chicago! - Oak Park, IL
9.4 71 reviews

Spacious Oak Park Home, 11 Mi To Downtown Chicago!

house, Oak Park
This comfortable house is situated in Oak Park, just 18 kilometres from downtown Chicago and 14 kilometres from the United Center, offering easy access to the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious three-bedroom home, spanning 223 square metres, comfortably accommodates up to six guests. The house boasts a well-equipped kitchen, laundry facilities, a garden, and parking, ensuring a comfortable and enjoyable stay.
Walk To Wrigley Field/monthly Discounts Available - Oak Park, IL
9.8 206 reviews

Walk To Wrigley Field/monthly Discounts Available

apartment, Chicago
This apartment is located in Lakeview, a lively neighbourhood just a short walk from Wrigley Field and across the street from the Metro, with easy access to the city's attractions. It has been highly rated by previous guests for its comfortable accommodation and excellent location.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. The kitchen is equipped with a fridge, microwave oven, and dishwasher, and the property also offers a terrace/balcony, garden, parking, and air conditioning.
Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12 - Oak Park, IL
10 5 reviews

Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12

apartment, Chicago
This West Town apartment, situated in Chicago, is conveniently located within a 5-8km radius of attractions such as Fulton Market, the United Centre, Grant Park, Michigan Avenue, and Lake Michigan.
Sleeping up to 12 guests, this three-bedroom, three-bathroom dwelling boasts a king suite with fireplace and steam shower, a queen suite with private roof deck access, a fully equipped kitchen with balcony, a private garage, and a stunning roof deck with Willis Tower views.

Best Oak Park, IL holiday rentals with air conditioning

Charming Retro 2br Cottage/train/laundry/free Pkg - Oak Park, IL
9.8 61 reviews

Charming Retro 2br Cottage/train/laundry/free Pkg

apartment, Oak Park
This charming retro cottage is located in Oak Park's Arts District, just a short walk from the Blue Line train station, providing easy access to downtown Chicago. The cottage is within 1 kilometre of Mills Park and Randolph Tot Lot, making it an ideal base for exploring Oak Park's attractions.
The cottage has two bedrooms and a living room, comfortably accommodating up to five guests. The kitchen is fully equipped with modern appliances and a private patio with bistro lights offers a relaxing outdoor space.
Studio Apartment In Oak Park - Oak Park, IL
9.9 132 reviews

Studio Apartment In Oak Park

studio, Oak Park
This Oak Park studio apartment is ideally situated in the historic district, mere steps from Ernest Hemingway's birthplace and a short walk (less than 0.5 km) from Frank Lloyd Wright's Home and Studio.
The self-contained unit, sleeping up to two guests, features a queen-sized bed, a compact kitchenette with fridge, freezer and microwave, a newly updated bathroom, and a private garden; nearby attractions include numerous cafes, shops, restaurants, a cinema and convenient access to CTA/Metra public transport.
4 Bed/1.5 Bath Townhouse In Flw Historic District! - Oak Park, IL
9.6 45 reviews

4 Bed/1.5 Bath Townhouse In Flw Historic District!

house, Oak Park
This four-bedroom duplex is located in Oak Park's Frank Lloyd Wright District, on the same street as the William E. Martin House, and is 0.8km from local restaurants and the Green Line 'L' train station.
This spacious 150m² property offers a comfortable home-from-home experience for up to seven guests, boasting a private garden, parking, and all modern amenities including a dishwasher and air conditioning.
Sunny Coach House In Historic Oak Park - Oak Park, IL
9.8 133 reviews

Sunny Coach House In Historic Oak Park

house, Oak Park
This Oak Park studio apartment is located in the Frank Lloyd Wright Historic District, a short walk from Chicago's downtown trains.
The self-contained unit, sleeping up to three guests, features a fridge, air conditioning, free parking, a private entrance, and access to a shared garden and fire pit; it's situated in a converted coach house behind a 1909 Prairie-style home.

Book Your Next Luxury Holiday Rental in Oak Park, IL, United States

Find luxury holiday rentals in Oak Park, IL, United States for a stylish, high-end city stay.

Comfortable Living, Within Reach! - Oak Park, IL
No reviews

Comfortable Living, Within Reach!

apartment, Oak Park

Browse Downtown Holiday Rentals in Oak Park, IL, United States

Spend less time navigating public transport and more time exploring attractions from central holiday rentals in Oak Park, IL, United States.

Good Sized 3 Br Apt. - Flw Hist. Dist. - Oak Park - Oak Park, IL
9.8 44 reviews

Good Sized 3 Br Apt. - Flw Hist. Dist. - Oak Park

apartment, Oak Park
Urban Oasis In The Heart Of Oak Park - Oak Park, IL
10 1 review

Urban Oasis In The Heart Of Oak Park

apartment, Oak Park
O'malley Oasis! - Oak Park, IL
9.9 145 reviews

O'malley Oasis!

house, Oak Park
1 Bedroom Apartment In Lovely Victorian House - Oak Park, IL
9.5 56 reviews

1 Bedroom Apartment In Lovely Victorian House

apartment, Oak Park
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