Guest house holiday rentals in Chicago
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Chicago
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Chicago
Guest house rentals with a patio
Guest house in Logan Square
Private Coach House / Easy Commute
Guest house in Villa Park
Tranquil Pondview + New Kitchen + King Bed + WFH
Guest house in Hyde Park
2 br, 2 bt, UChicago Coachman's Guesthouse
Guest house in Logan Square
MultiManor: A Renovated Bucktown Coach House
Guest house in Wheaton
Guesthouse Adjacent to Wheaton College
Guest house in Gary
Farm Themed Guesthouse! (NEW)
Guest house in Avondale
Botanical BnB. House in Avondale/Logan Square.
Guest house in Logan Square
Logan Square Coach House
Guest house rentals with a washing machine and dryer
Guest house in Avondale
Quiet, Cozy 1-Bedroom Carriage House in Chicago
Guest house in Oak Park
Stylish Coachhouse in lovely Oak Park!
Guest house in Evanston
Cozy Guesthouse near NU - next to Lee Street Beach
Guest house in Humboldt Park
Hidden Cottage in Logan Square
Guest house in Arlington Heights
Cozy Chicago Suburban Apartment
Guest house in West Town
Charming private coach house
Guest house in Wicker Park
Private Historic Coach House Wicker Park
Guest house in Evanston
Historic Coach House in Evanston Near Beach & Town
Quick stats about guest house 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
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Guest house rentals United States
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