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Guesthouse vacation rentals in Cook County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Cook County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cook County guesthouse rentals
Family-friendly guest house rentals
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Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsCoach House, Dunes Nat’l Park, 10min hike to Beach
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Guesthouse in Wheaton
4.95 out of 5 average rating, 403 reviewsCozy private coach house in Wheaton
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Guesthouse in Oak Park
4.88 out of 5 average rating, 466 reviewsCoachhouse in central OP 4 blk to L
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Guesthouse in Chicago
4.88 out of 5 average rating, 258 reviewsThe Rectory
Guest house rentals with a patio
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Guesthouse in Villa Park
4.83 out of 5 average rating, 48 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
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Guesthouse in Merrillville
4.87 out of 5 average rating, 39 reviewsTownhouse/ Guesthouse with Jacuzzi/Sauna/Pool
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Guesthouse in Chicago
5 out of 5 average rating, 43 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
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Guesthouse in Chicago
4.95 out of 5 average rating, 20 reviewsPrivate Coach House / Easy Commute
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Guesthouse in Chicago
5 out of 5 average rating, 5 reviewsCozy 2 bed Garden unit 5 minutes to Midway Airport
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Guesthouse in Chicago
4.97 out of 5 average rating, 31 reviewsMultiManor: A Renovated Bucktown Coach House
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Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
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Guesthouse in Chicago
5 out of 5 average rating, 4 reviewsSolar Victorian MCM Coach House
Guest house rentals with a washer and dryer
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Guesthouse in Villa Park
4.91 out of 5 average rating, 86 reviewsEclectic Coach House Apartment
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Guesthouse in Oak Park
4.99 out of 5 average rating, 79 reviewsStylish Coachhouse in lovely Oak Park!
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Guesthouse in Evanston
4.91 out of 5 average rating, 80 reviewsCozy Guesthouse near NU - next to Lee Street Beach
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Guesthouse in Chicago
4.95 out of 5 average rating, 95 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
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Guesthouse in Arlington Heights
4.93 out of 5 average rating, 28 reviewsCozy Chicago Suburban Apartment
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Guesthouse in Chicago
4.88 out of 5 average rating, 75 reviewsHidden Cottage in Logan Square
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Guesthouse in Chicago
4.93 out of 5 average rating, 89 reviewsModern Chicago Home Away from Home
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Guesthouse in Chicago
4.94 out of 5 average rating, 34 reviewsCharming private coach house
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