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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.

Entire guesthouse · Oak Park
O'Malley Oasis!
Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!
$131 per night
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Entire rental unit · Oak Park
Sunny Jumbo Studio in the Heart of Oak Park
Bright and sunny Oak Park jumbo 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 double bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!
$88 per night
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Entire guest suite · Oak Park
Clean, Modern Studio in Historic Oak Park
Located in historic Oak Park, a short ride to Chicago, this basement studio is perfect for the tourist, family or business traveler. This rental is NOT the entire house, but a unit with a separate entrance. Enjoy the privacy of a remodeled, beautiful studio while appreciating historic architecture nearby. With multiple Historic Landmark homes nearby (including one right next door), our 1923 Tudor is the perfect home base when Chicagoland is your destination.
$125 per night
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Stay near Oak Park's top sights

Photo of Frank Lloyd Wright Home and Studio
Frank Lloyd Wright Home and Studio81 locals recommend
Photo of Oak Park Conservatory
Oak Park Conservatory12 locals recommend
Photo of Classic Cinemas Lake Theatre
Classic Cinemas Lake Theatre40 locals recommend
Photo of Poor Phil's Bar and Grill
Poor Phil's Bar and Grill10 locals recommend
Photo of Oak Park Public Library - Main Library
Oak Park Public Library - Main Library12 locals recommend
Photo of Mills Park
Mills Park3 locals recommend

Other great vacation rentals in Oak Park

Entire rental unit · Oak Park
Long stays welcome@warm&cute vintage 2BR
$130 per night
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Entire guesthouse · Oak Park
Coachhouse in central OP 4 blk to L
$118 per night
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Private room · Oak Park
Victorian Gem in Heart of FLW District
$90 per night
Private room · Forest Park
4J1 Garden flr bedroom near Chicago & Loyola
$55 per night
Entire rental unit · Oak Park
1BR Apartment - Walk to Shops - Downtown OAK PARK
$113 per night
Entire rental unit · Oak Park
1 bed 1 bath apartment 42-2
$84 per night
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Entire guesthouse · Oak Park
1 Bdrm Coach House - Frank Lloyd Wright District
$95 per night
Entire condo · Oak Park
Cozy condo Oak Park
$72 per night
Entire guesthouse · Oak Park
Sunny Coach House in Historic Oak Park
$112 per night
Private room · Oak Park
Antique Filled Home
$65 per night
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Entire rental unit · Oak Park
Cosmopolitan nest in Oak Parks North Side
$68 per night
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Entire condo · Oak Park
Peaceful Oak Park Condo Next to Green Line Metro
$177 per night
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