Guesthouse vacation rentals in North Side
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Top-rated guesthouses in North Side
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses
Guesthouse in Wheaton
4.95 out of 5 average rating, 385 reviewsCozy private coach house in Wheaton
Oct. 27 – Nov. 3
Guesthouse in Oak Park
4.88 out of 5 average rating, 456 reviewsCoachhouse in central OP 4 blk to L
Oct. 23 – 30
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
Aug. 17 – 24
Guesthouses with a patio
Guesthouse in Villa Park
4.83 out of 5 average rating, 40 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Aug. 21 – 28
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
Oct. 1 – 8
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Aug. 30 – Sep. 6
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
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Aug. 28 – Sep. 4
Guesthouse rentals with a washer and dryer
Guesthouse in Oak Park
4.99 out of 5 average rating, 72 reviewsStylish Coachhouse in lovely Oak Park!
Feb. 14 – 21
Guesthouse in Villa Park
4.92 out of 5 average rating, 72 reviewsEclectic Coach House Apartment
Jan. 29 – Feb. 5
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
Feb. 16 – 23
Guesthouse in Chicago
4.9 out of 5 average rating, 50 reviewsCharming Logan Square Coach House
Aug. 12 – 19
Guesthouse in Lake Forest
4.95 out of 5 average rating, 96 reviewsThe Green Door - safe and calm with walkability
Feb. 26 – Mar. 5
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Dec. 17 – 24
Guesthouse in Chicago
4.94 out of 5 average rating, 32 reviewsCharming private coach house
Sep. 19 – 26
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