Guesthouse vacation rentals in West Side
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in West Side
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 West Side guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Wheaton
4.95 out of 5 average rating, 390 reviewsCozy private coach house in Wheaton
Guesthouse in Chicago
4.95 out of 5 average rating, 368 reviewsCozy Coach House
Guesthouse in Oak Park
4.88 out of 5 average rating, 458 reviewsCoachhouse in central OP 4 blk to L
Guesthouse in Chicago
4.88 out of 5 average rating, 252 reviewsThe Rectory
Guest house rentals with a patio
Guesthouse in Villa Park
4.84 out of 5 average rating, 44 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Guesthouse in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
Guesthouse in Chicago
5.0 out of 5 average rating, 27 reviewsMultiManor: A Renovated Bucktown Coach House
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Guesthouse in Chicago
4.94 out of 5 average rating, 18 reviewsLogan Square Coach House
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Guest house rentals with a washer and dryer
Guesthouse in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
Guesthouse in Chicago
4.94 out of 5 average rating, 86 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Guesthouse in Villa Park
4.92 out of 5 average rating, 78 reviewsEclectic Coach House Apartment
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Guesthouse in Evanston
4.91 out of 5 average rating, 77 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse in Chicago
4.93 out of 5 average rating, 84 reviewsModern Chicago Home Away from Home
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