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
Jan 21 – 28
Guesthouse in Wheaton
4.95 out of 5 average rating, 386 reviewsCozy private coach house in Wheaton
Nov 27 – Dec 4
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug 19 – 26
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Oct 30 – Nov 6
Guesthouse in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
Nov 3 – 10
Guest house rentals with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 41 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Aug 16 – 23
Guesthouse in Merrillville
4.93 out of 5 average rating, 27 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Dec 26 – Jan 2
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
Jun 29 – Jul 6
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Oct 11 – 18
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Aug 31 – Sep 7
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Oct 24 – 31
Guest house rentals with a washer and dryer
Guesthouse in Oak Park
4.99 out of 5 average rating, 73 reviewsStylish Coachhouse in lovely Oak Park!
Oct 18 – 25
Guesthouse in Chicago
4.94 out of 5 average rating, 83 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Oct 20 – 27
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Apr 9 – 16
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
May 9 – 14
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
Mar 31 – Apr 7
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Dec 4 – 11
Guesthouse in Evanston
4.94 out of 5 average rating, 97 reviewsHistoric Coach House in Evanston Near Beach & Town
Sep 25 – Oct 2
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
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