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
4.89 out of 5 average rating, 484 reviewsCoachhouse in central OP 4 blk to L
Guest house
4.87 out of 5 average rating, 279 reviewsThe Rectory
Guest house
4.95 out of 5 average rating, 407 reviewsCozy Coach House
Guest house
4.95 out of 5 average rating, 439 reviewsCozy private coach house in Wheaton
Guest house
4.94 out of 5 average rating, 168 reviewsCoach House Art Studio, By Downtown & Northwestern
Guest house rentals with a patio
Guest house
4.9 out of 5 average rating, 42 reviewsLogan Square Coach House
Guest house
4.96 out of 5 average rating, 27 reviewsSolar Victorian MCM Coach House
Guest house
4.98 out of 5 average rating, 66 reviewsBotanical BnB. House in Avondale/Logan Square.
Guest house
5 out of 5 average rating, 3 reviewsGuesthouse Adjacent to Wheaton College
Guest house
4.93 out of 5 average rating, 14 reviewsGreen #3
Guest house
4 out of 5 average rating, 6 reviewsCozy and Private Home
Guest house
4.86 out of 5 average rating, 70 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guest house
5 out of 5 average rating, 61 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
Guest house rentals with a washing machine and dryer
Guest house
5 out of 5 average rating, 25 reviewsMitra Guest House
Guest house
4.93 out of 5 average rating, 44 reviewsCozy Chicago Suburban Apartment
Guest house
4.88 out of 5 average rating, 58 reviewsHome Sweet Home
Guest house
4.92 out of 5 average rating, 96 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guest house
4.95 out of 5 average rating, 41 reviewsCharming private coach house
Guest house
4.98 out of 5 average rating, 88 reviewsPrivate Historic Coach House Wicker Park
Guest house
4.9 out of 5 average rating, 89 reviewsHidden Cottage in Logan Square
Guest house
4.85 out of 5 average rating, 13 reviewsWhimsical Cottage......Brand new construction
Quick stats about guest house rentals in Chicago
Total rentals
70 properties
Total number of reviews
7.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
Destinations to explore
- Downtown Chicago Holiday rentals
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