Guesthouse vacation rentals in Cook County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Cook County
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 Cook County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Miller Beach
4.17 out of 5 average rating, 29 reviewsDream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Oct 28 – Nov 4
Guesthouse in Wheaton
4.95 out of 5 average rating, 388 reviewsCozy private coach house in Wheaton
Feb 19 – 26
Guesthouse in Oak Park
4.88 out of 5 average rating, 457 reviewsCoachhouse in central OP 4 blk to L
Feb 6 – 13
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
Oct 17 – 24
Guest house rentals with a patio
Guesthouse in Merrillville
4.93 out of 5 average rating, 30 reviewsTownhouse with Jacuzzi/Sauna/fireplace
Jan 10 – 17
Guesthouse in Chicago
4.92 out of 5 average rating, 13 reviewsPrivate Coach House / Easy Commute
Sep 11 – 18
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
Aug 11 – 18
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
Jan 6 – 13
Guesthouse in Chicago
4.94 out of 5 average rating, 17 reviewsLogan Square Coach House
Sep 9 – 16
Guesthouse in Chicago
4.75 out of 5 average rating, 36 reviewsHistoric Washington-Hyde Park Greystone
Sep 5 – 12
Guesthouse in Chicago
4.98 out of 5 average rating, 41 reviewsBotanical BnB. House in Avondale/Logan Square.
Oct 26 – Nov 2
Guest house rentals with a washer and dryer
Guesthouse in Oak Park
4.99 out of 5 average rating, 73 reviewsStylish Coachhouse in lovely Oak Park!
Oct 30 – Nov 6
Guesthouse in Arlington Heights
4.91 out of 5 average rating, 23 reviewsCozy Chicago Suburban Apartment
Feb 21 – 28
Guesthouse in Evanston
4.91 out of 5 average rating, 76 reviewsCozy Guesthouse near NU - next to Lee Street Beach
Jan 29 – Feb 5
Guesthouse in Chicago
4.94 out of 5 average rating, 85 reviewsQuiet, Cozy 1-Bedroom Carriage House in Chicago
Sep 11 – 18
Guesthouse in Chicago
4.88 out of 5 average rating, 72 reviewsHidden Cottage in Logan Square
May 9 – 14
Guesthouse in Evanston
4.94 out of 5 average rating, 97 reviewsHistoric Coach House in Evanston Near Beach & Town
Sep 21 – 28
Guesthouse in Chicago
4.93 out of 5 average rating, 84 reviewsModern Chicago Home Away from Home
Jul 11 – 18
Guesthouse in Chicago
4.97 out of 5 average rating, 79 reviewsPrivate Historic Coach House Wicker Park
Aug 21 – 28
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals Chicago
- House rentals Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- Guesthouse rentals Illinois
- House rentals Illinois
- Beachfront rentals Cook County
- Rentals with a washer and dryer Cook County
- Rentals with an accessible height toilet Cook County
- Kid-friendly rentals Cook County
- Townhouse rentals Cook County
- Apartment rentals Cook County
- Smoking-friendly rentals Cook County
- Fitness-friendly rentals Cook County
- Monthly Rentals Cook County
- House rentals Cook County
- Rentals with an EV charger Cook County
- Bed and breakfasts Cook County
- Boutique hotel rentals Cook County
- Waterfront rentals Cook County
- Rentals with a soaking tub Cook County
- Loft rentals Cook County
- Rentals with a balcony Cook County
- Rentals with a home theater Cook County
- Rentals with a patio Cook County
- Rentals with a hot tub Cook County
- Rentals with a kayak Cook County
- Pet-friendly rentals Cook County
- Condo rentals Cook County
- Rentals with a fire pit Cook County
- Family-friendly rentals Cook County
- Hotel rentals Cook County
- Rentals with a sauna Cook County
- Rentals with outdoor seating Cook County
- Rentals with beach access Cook County
- Rentals with a fireplace Cook County
- Rentals with pools Cook County
- Rentals with breakfast Cook County
- Rentals with an accessible height bed Cook County
- Rentals with lake access Cook County
- Private suite 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