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 Wheaton
4.95 out of 5 average rating, 386 reviewsCozy private coach house in Wheaton
Jan 4 – 11
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug 19 – 26
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Nov 3 – 10
Guesthouse in Chicago
4.88 out of 5 average rating, 251 reviewsThe Rectory
Aug 17 – 24
Guest house rentals with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 41 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Aug 21 – 28
Guesthouse in Merrillville
4.93 out of 5 average rating, 27 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Nov 3 – 10
Guesthouse in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
Sep 14 – 21
Guesthouse in Chicago
5.0 out of 5 average rating, 34 reviews2 br, 2 bt, detached, UChicago Coachman's House
Dec 29 – Jan 5
Guesthouse in Chicago
5.0 out of 5 average rating, 26 reviewsMultiManor: A Renovated Bucktown Coach House
Aug 16 – 23
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Sep 30 – Oct 7
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Nov 10 – 17
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Oct 24 – 31
Guest house rentals with a washer and dryer
Guesthouse in Chicago
4.94 out of 5 average rating, 82 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Sep 15 – 22
Guesthouse in Oak Park
4.99 out of 5 average rating, 72 reviewsStylish Coachhouse in lovely Oak Park!
Jan 12 – 19
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Dec 11 – 18
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
Feb 28 – Mar 7
Guesthouse in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
Aug 12 – 19
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Sep 19 – 26
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
May 9 – 14
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
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Guesthouse rentals United States
- House rentals United States
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Condo rentals Chicago
- Hotel rentals Chicago
- Rentals with a home theater Chicago
- Beachfront rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a sauna Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a washer and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Mansion rentals Chicago
- Rentals with a patio Chicago
- Apartment rentals Chicago
- Lakehouse rentals Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- Rentals with beach access Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- House rentals Illinois
- Guesthouse rentals Illinois
- Guesthouse 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