Guesthouse vacation rentals in Cook County
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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
Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsDream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Oct 31 – Nov 7
Guesthouse in Wheaton
4.95 out of 5 average rating, 388 reviewsCozy private coach house in Wheaton
Apr 1 – 8
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Feb 6 – 13
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug 19 – 26
Guesthouse in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
Jul 10 – 17
Guest house rentals with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 42 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Oct 19 – 26
Guesthouse in Merrillville
4.93 out of 5 average rating, 28 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Dec 30 – Jan 6
Guesthouse in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
Sep 11 – 18
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Dec 29 – Jan 5
Guesthouse in Chicago
5.0 out of 5 average rating, 27 reviewsMultiManor: A Renovated Bucktown Coach House
Sep 13 – 20
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Jan 5 – 12
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Sep 9 – 16
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Oct 20 – 27
Guest house rentals with a washer and dryer
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Mar 22 – 29
Guesthouse in Chicago
4.94 out of 5 average rating, 84 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Sep 28 – Oct 5
Guesthouse in Evanston
4.94 out of 5 average rating, 97 reviewsHistoric Coach House in Evanston Near Beach & Town
Sep 20 – 27
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 23 reviewsCozy Chicago Suburban Apartment
Apr 6 – 13
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
May 9 – 14
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Nov 10 – 17
Guesthouse in Chicago
4.93 out of 5 average rating, 84 reviewsModern Chicago Home Away from Home
Jul 10 – 17
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