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 reviewsDream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Mar 1 – 8
Guesthouse in Wheaton
4.95 out of 5 average rating, 387 reviewsCozy private coach house in Wheaton
Sep 25 – Oct 2
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Nov 8 – 15
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug 19 – 26
Guesthouse in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
Aug 18 – 25
Guest house rentals with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 42 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Oct 1 – 8
Guesthouse in Merrillville
4.93 out of 5 average rating, 28 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Aug 9 – 16
Guesthouse in Chicago
5.0 out of 5 average rating, 36 reviews2 br, 2 bt, detached, UChicago Coachman's House
Dec 29 – Jan 5
Guesthouse in Chicago
5.0 out of 5 average rating, 27 reviewsMultiManor: A Renovated Bucktown Coach House
Aug 4 – 11
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Jan 3 – 10
Guesthouse in Carpentersville
5.0 out of 5 average rating, 3 reviews1 bedroom guest house
Jan 22 – 29
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Sep 9 – 16
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Oct 25 – Nov 1
Guest house rentals with a washer and dryer
Guesthouse in Chicago
4.94 out of 5 average rating, 84 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Oct 15 – 22
Guesthouse in Villa Park
4.92 out of 5 average rating, 73 reviewsEclectic Coach House Apartment
Nov 15 – 22
Guesthouse in Oak Park
4.99 out of 5 average rating, 73 reviewsStylish Coachhouse in lovely Oak Park!
Mar 26 – Apr 2
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Oct 29 – Nov 5
Guesthouse in Lake Forest
4.95 out of 5 average rating, 96 reviewsThe Green Door - safe and calm with walkability
Apr 7 – 14
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
Feb 25 – Mar 4
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Sep 11 – 18
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
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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