Guest house holiday rentals in Cook County
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Top-rated guest house rentals in Cook County
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for guest house rentals in Cook County
Family-friendly guest house rentals
Guest house in Miller Beach
4.17 out of 5 average rating, 29 reviewsDream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
20–27 Dec
Guest house in Wheaton
4.95 out of 5 average rating, 386 reviewsCozy private coach house in Wheaton
27 Oct – 3 Nov
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
23–30 Oct
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
15–22 May
Guest house in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
14–21 Sept
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
1–8 Oct
Guest house in Wheaton
Guesthouse Adjacent to Wheaton College
30 Aug – 6 Sept
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
3–10 Sept
Guest house in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
16–23 Feb
Guest house in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
9–14 May
Guest house in Arlington Heights
4.91 out of 5 average rating, 22 reviewsCozy Chicago Suburban Apartment
7–14 Apr
Guest house in Evanston
4.94 out of 5 average rating, 96 reviewsHistoric Coach House in Evanston Near Beach & Town
12–19 Sept
Guest house in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
17–24 Dec
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 Sept
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