Guesthouse vacation rentals in Chicago
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Chicago
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 Chicago guesthouse rentals
Family-friendly guest house rentals
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, 397 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
4.88 out of 5 average rating, 253 reviewsThe Rectory
Guest house rentals with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 48 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Merrillville
4.84 out of 5 average rating, 32 reviewsTownhouse/ Guesthouse with Jacuzzi/Sauna/Pool
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
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, 5 reviewsFarm Themed Guesthouse! (NEW)
Guesthouse in Chicago
4.98 out of 5 average rating, 44 reviewsBotanical BnB. House in Avondale/Logan Square.
Guesthouse in Chicago
4.95 out of 5 average rating, 19 reviewsLogan Square Coach House
Guest house rentals with a washer and dryer
Guesthouse in Chicago
4.94 out of 5 average rating, 90 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guesthouse in Oak Park
4.99 out of 5 average rating, 77 reviewsStylish Coachhouse in lovely Oak Park!
Guesthouse in Evanston
4.91 out of 5 average rating, 78 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse in Lake Forest
4.95 out of 5 average rating, 98 reviewsThe Green Door - safe and calm with walkability
Guesthouse in Villa Park
4.9 out of 5 average rating, 82 reviewsEclectic Coach House Apartment
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, 33 reviewsCharming private coach house
Guesthouse in Chicago
4.88 out of 5 average rating, 74 reviewsHidden Cottage in Logan Square
Quick stats about guesthouse rentals in Chicago
Total rentals
70 properties
Wifi availability
70 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
6.6K reviews
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