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, 386 reviewsCozy private coach house in Wheaton
4–11 Jan
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, 457 reviewsCoachhouse in central OP 4 blk to L
3–10 Nov
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, 41 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
21–28 Aug
Guest house in Merrillville
4.93 out of 5 average rating, 27 reviewsTownhouse with Jacuzzi/Sauna/fireplace
3–10 Nov
Guest house in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
14–21 Sep
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
16–23 Aug
Guest house in Wheaton
Guesthouse Adjacent to Wheaton College
30 Sep – 7 Oct
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
15–22 Sep
Guest house in Oak Park
4.99 out of 5 average rating, 72 reviewsStylish Coachhouse in lovely Oak Park!
12–19 Jan
Guest house in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
11–18 Dec
Guest house in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
28 Feb – 7 Mar
Guest house in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
12–19 Aug
Guest house in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
19–26 Sep
Guest house in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
21–28 Aug
Guest house in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
9–14 May
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
- House rentals United States
- Pet-friendly rentals Chicago
- Villa rentals Chicago
- Rentals with beach access Chicago
- Rentals with a sauna Chicago
- Rentals with an EV charger Chicago
- Waterfront rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a cinema Chicago
- Rentals with a patio Chicago
- Hotel rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Fitness-friendly rentals Chicago
- Apartment rentals Chicago
- Family-friendly rentals Chicago
- Loft rentals Chicago
- Cottage rentals Chicago
- Beachfront rentals Chicago
- Flat rentals Chicago
- Rentals with pools Chicago
- Lakehouse rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with breakfast Chicago
- House rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a fireplace Chicago
- Boutique hotel rentals Chicago
- Monthly Rentals Chicago
- Rentals with lake access Chicago
- Mansion rentals Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Private suite rentals Chicago
- Family-friendly rentals Chicago
- Rentals with an accessible-height bed Chicago
- Smoking-friendly rentals Chicago
- Townhouse rentals Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- Guest house rentals Illinois
- House rentals Illinois
- Guest house rentals Cook County
- House rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom