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
Family-friendly guest house rentals
Guest house in Miller Beach
4.17 out of 5 average rating, 29 reviewsCoach House, Dunes Nat’l Park, 10min hike to Beach
Guest house in Wheaton
4.95 out of 5 average rating, 397 reviewsCozy private coach house in Wheaton
Guest house in Oak Park
4.88 out of 5 average rating, 461 reviewsCoachhouse in central OP 4 blk to L
Guest house in Chicago
4.88 out of 5 average rating, 252 reviewsThe Rectory
Guest house in Chicago
4.95 out of 5 average rating, 372 reviewsCozy Coach House
Guest house rentals with a patio
Guest house in Chicago
4.93 out of 5 average rating, 15 reviewsPrivate Coach House / Easy Commute
Guest house in Villa Park
4.83 out of 5 average rating, 47 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guest house in Merrillville
4.93 out of 5 average rating, 30 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Guest house in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Guest house in Chicago
5.0 out of 5 average rating, 28 reviewsMultiManor: A Renovated Bucktown Coach House
Guest house in Wheaton
Guesthouse Adjacent to Wheaton College
Guest house in Chicago
4.94 out of 5 average rating, 18 reviewsLogan Square Coach House
Guest house in Chicago
4.98 out of 5 average rating, 43 reviewsBotanical BnB. House in Avondale/Logan Square.
Guest house rentals with a washing machine and dryer
Guest house in Chicago
4.94 out of 5 average rating, 89 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Guest house in Villa Park
4.9 out of 5 average rating, 81 reviewsEclectic Coach House Apartment
Guest house in Oak Park
4.99 out of 5 average rating, 76 reviewsStylish Coachhouse in lovely Oak Park!
Guest house in Lake Forest
4.95 out of 5 average rating, 98 reviewsThe Green Door - safe and calm with walkability
Guest house in Evanston
4.91 out of 5 average rating, 77 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guest house in Arlington Heights
4.92 out of 5 average rating, 25 reviewsCozy Chicago Suburban Apartment
Guest house in Chicago
4.94 out of 5 average rating, 33 reviewsCharming private coach house
Guest house in Chicago
4.88 out of 5 average rating, 73 reviewsHidden Cottage in Logan Square
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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- Rentals with an EV charger Chicago
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