Guesthouse vacation rentals in North Side
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Top-rated guesthouse rentals in North Side
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 North Side guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Wheaton
4.95 out of 5 average rating, 387 reviewsCozy private coach house in Wheaton
Dec 10 – 17
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Apr 22 – 29
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
Sep 6 – 13
Guest house rentals with a patio
Guesthouse in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
Sep 11 – 18
Guesthouse in Villa Park
4.83 out of 5 average rating, 42 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Sep 16 – 23
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
Sep 10 – 17
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Dec 19 – 26
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Sep 1 – 8
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Nov 16 – 23
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 Villa Park
4.92 out of 5 average rating, 72 reviewsEclectic Coach House Apartment
Feb 1 – 8
Guesthouse in Oak Park
4.99 out of 5 average rating, 73 reviewsStylish Coachhouse in lovely Oak Park!
Mar 6 – 13
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
May 9 – 14
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Mar 9 – 16
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
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
Dec 4 – 11
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
Oct 20 – 27
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