Guesthouse holiday rentals in Cook County
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Cook County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Cook County guesthouses
Family-Friendly guesthouses
Guesthouse in Oak Park
4.89 out of 5 average rating, 482 reviewsCoachhouse in central OP 4 blk to L
Guesthouse in Chicago
4.95 out of 5 average rating, 403 reviewsCozy Coach House
Guesthouse in Chicago
4.87 out of 5 average rating, 277 reviewsThe Rectory
Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsCoach House, Dunes Nat’l Park, 10min hike to Beach
Guesthouse in Wheaton
4.95 out of 5 average rating, 434 reviewsCozy private coach house in Wheaton
Guesthouse in Evanston
4.94 out of 5 average rating, 167 reviewsCoach House Art Studio, By Downtown & Northwestern
Guesthouses with a patio
Guesthouse in Merrillville
4.91 out of 5 average rating, 65 reviewsGuesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Guesthouse in Chicago
4.96 out of 5 average rating, 25 reviewsSolar Victorian MCM Coach House
Guesthouse in Chicago
4.98 out of 5 average rating, 62 reviewsBotanical BnB. House in Avondale/Logan Square.
Guesthouse in Chicago
4.6 out of 5 average rating, 5 reviewsCozy and Private Home
Guesthouse in Villa Park
4.85 out of 5 average rating, 68 reviewsTranquil Pondview + New Kitchen + King Bed + WFH
Guesthouse in Gary
4.97 out of 5 average rating, 37 reviewsFarm Themed Guesthouse!
Guesthouse in Chicago
5 out of 5 average rating, 58 reviews2 br, 2 bt, UChicago Coachman's Guesthouse
Guest house rentals with a washing machine and dryer
Guesthouse in Evanston
5 out of 5 average rating, 24 reviewsMitra Guest House
Guesthouse in Chicago
4.88 out of 5 average rating, 57 reviewsHome Sweet Home
Guesthouse in Arlington Heights
4.95 out of 5 average rating, 41 reviewsCozy Chicago Suburban Apartment
Guesthouse in Evanston
4.92 out of 5 average rating, 95 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Guesthouse in Chicago
4.99 out of 5 average rating, 827 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Guesthouse in Chicago
4.98 out of 5 average rating, 88 reviewsPrivate Historic Coach House Wicker Park
Guesthouse in Chicago
4.9 out of 5 average rating, 89 reviewsHidden Cottage in Logan Square
Guesthouse in Oak Park
4.99 out of 5 average rating, 98 reviewsStylish Coachhouse in lovely Oak Park!
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- House rentals Illinois
- Guesthouse rentals Illinois
- Rentals with pools Cook County
- Rentals with an EV charger Cook County
- Waterfront rentals Cook County
- Rentals with an accessible height toilet Cook County
- Rentals with a fire pit Cook County
- Rentals with a sauna Cook County
- Rentals with beach access Cook County
- Private suite rentals Cook County
- Rentals with a balcony Cook County
- Pet-friendly rentals Cook County
- Hotel rentals Cook County
- Townhouse rentals Cook County
- Rentals with a washing machine and dryer Cook County
- Rentals with an accessible height bed Cook County
- Fitness-friendly rentals Cook County
- Smoking-friendly rentals Cook County
- Bed and breakfasts Cook County
- Rentals with a fireplace Cook County
- Rentals with a hot tub Cook County
- Rentals with a kayak Cook County
- Apartment rentals Cook County
- Loft rentals Cook County
- Condo rentals Cook County
- Rentals with a patio Cook County
- Rentals with a home theatre Cook County
- Rentals with lake access Cook County
- Family-friendly rentals Cook County
- Kid-friendly rentals Cook County
- Monthly Rentals Cook County
- Beachfront rentals Cook County
- Rentals with outdoor seating Cook County
- Rentals with breakfast 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
- Things to do United States
- Sports activities United States
- Wellness United States
- Food and drink United States
- Entertainment United States
- Sightseeing United States
- Art and culture United States
- Nature and outdoors United States
- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County