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 Wheaton
4.95 out of 5 average rating, 385 reviewsCozy private coach house in Wheaton
27 Oct – 3 Nov
Guest house in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
19–26 Aug
Guest house in Oak Park
4.88 out of 5 average rating, 456 reviewsCoachhouse in central OP 4 blk to L
23–30 Oct
Guest house in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
17–24 Aug
Guest house rentals with a patio
Guest house in Villa Park
4.83 out of 5 average rating, 40 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
21–28 Aug
Guest house in Merrillville
4.92 out of 5 average rating, 25 reviewsTownhouse with Jacuzzi/Sauna/fireplace
15–22 May
Guest house in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
14–21 Sept
Guest house in Chicago
5.0 out of 5 average rating, 34 reviews2 br, 2 bt, detached, UChicago Coachman's House
29 Dec – 5 Jan
Guest house in Chicago
5.0 out of 5 average rating, 26 reviewsMultiManor: A Renovated Bucktown Coach House
1–8 Oct
Guest house in Wheaton
Guesthouse Adjacent to Wheaton College
30 Aug – 6 Sept
Guest house in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
10–17 Nov
Guest house in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
24–31 Oct
Guest house rentals with a washing machine and dryer
Guest house in Chicago
4.94 out of 5 average rating, 82 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
3–10 Sept
Guest house in Oak Park
4.99 out of 5 average rating, 72 reviewsStylish Coachhouse in lovely Oak Park!
14–21 Feb
Guest house in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
16–23 Feb
Guest house in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
12–19 Aug
Guest house in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
17–24 Dec
Guest house in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
19–26 Sept
Guest house in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
9–14 May
Guest house in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
7–14 Apr
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
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