Guesthouse vacation rentals in Cook County

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Cook County guesthouse rentals

Guest house rentals with a patio

Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in Oak Park

4.99 out of 5 average rating, 73 reviews

Stylish Coachhouse in lovely Oak Park!

Mar 6 – 13

G$26,742 GYD per night
Guest favorite

Guesthouse in Arlington Heights

4.91 out of 5 average rating, 22 reviews

Cozy Chicago Suburban Apartment

Oct 20 – 27

G$18,353 GYD per night
Guest favorite

Guesthouse in Chicago

4.94 out of 5 average rating, 84 reviews

Quiet, Cozy 1-Bedroom Carriage House in Chicago

Aug 19 – 26

G$32,197 GYD per night
Guest favorite

Guesthouse in Evanston

4.91 out of 5 average rating, 76 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

Apr 9 – 16

G$33,427 GYD per night
Guest favorite

Guesthouse in Chicago

4.88 out of 5 average rating, 72 reviews

Hidden Cottage in Logan Square

May 9 – 14

G$34,887 GYD per night
Guest favorite

Guesthouse in Evanston

4.94 out of 5 average rating, 97 reviews

Historic Coach House in Evanston Near Beach & Town

Sep 16 – 23

G$67,609 GYD per night
Guest favorite

Guesthouse in Chicago

4.94 out of 5 average rating, 32 reviews

Charming private coach house

Dec 4 – 11

G$38,585 GYD per night
Guest favorite

Guesthouse in Chicago

4.97 out of 5 average rating, 79 reviews

Private Historic Coach House Wicker Park

Aug 21 – 28

G$66,222 GYD per night

Destinations to explore