Guesthouse vacation rentals in Cook County
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Top-rated guesthouses in Cook County
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses
Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsCoach House, Dunes Nat’l Park, 10min hike to Beach
Guesthouse in Wheaton
4.95 out of 5 average rating, 399 reviewsCozy private coach house in Wheaton
Guesthouse in Oak Park
4.88 out of 5 average rating, 463 reviewsCoachhouse in central OP 4 blk to L
Guesthouse in Chicago
4.87 out of 5 average rating, 255 reviewsThe Rectory
Guesthouses with a patio
Guesthouse in Merrillville
4.86 out of 5 average rating, 35 reviewsTownhouse/ Guesthouse with Jacuzzi/Sauna/Pool
Guesthouse in Villa Park
4.83 out of 5 average rating, 48 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsPrivate Coach House / Easy Commute
Guesthouse in Chicago
5.0 out of 5 average rating, 38 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
Guesthouse in Chicago
5.0 out of 5 average rating, 28 reviewsMultiManor: A Renovated Bucktown Coach House
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Guesthouse in Gary
5.0 out of 5 average rating, 7 reviewsFarm Themed Guesthouse! (NEW)
Guesthouse in Northbrook
5.0 out of 5 average rating, 3 reviewsGreen #3
Guesthouse rentals with a washer and dryer
Guesthouse in Arlington Heights
4.92 out of 5 average rating, 26 reviewsCozy Chicago Suburban Apartment
Guesthouse in Chicago
4.94 out of 5 average rating, 90 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guesthouse in Chicago
4.88 out of 5 average rating, 75 reviewsHidden Cottage in Logan Square
Guesthouse in Chicago
4.93 out of 5 average rating, 86 reviewsModern Chicago Home Away from Home
Guesthouse in Chicago
4.94 out of 5 average rating, 34 reviewsCharming private coach house
Guesthouse in Chicago
4.98 out of 5 average rating, 80 reviewsPrivate Historic Coach House Wicker Park
Guesthouse in Glenview
4.76 out of 5 average rating, 21 reviewsSecluded guest house/inlaw apartment with parking
Guesthouse in Chicago
4.87 out of 5 average rating, 54 reviewsHome Sweet Home
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