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.

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Guest favourite

Guest house

4.94 out of 5 average rating, 113 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house . Extra

Guest favourite

Guest house

4.98 out of 5 average rating, 229 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Guest favourite

Guest house

4.96 out of 5 average rating, 114 reviews

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

Guest favourite

Guest house

4.98 out of 5 average rating, 267 reviews

Entire private coach house near transit, nightlife

This newly renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

Superhost

Guest house

4.91 out of 5 average rating, 341 reviews

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

Guest favourite

Guest house

4.89 out of 5 average rating, 274 reviews

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, Ravenswood, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or just crack open a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 2 miles north of Wrigley. Pets Allowed!

Guest favourite

Guest house

4.92 out of 5 average rating, 110 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

Guest favourite

Guest house

4.96 out of 5 average rating, 117 reviews

Quiet, Cozy 1-Bedroom Carriage House in Chicago

Quiet and private stand-alone carriage house in Chicago's hip Logan Square neighborhood! Perfect for traveling solo, working remotely, or a couple's getaway to the Windy City! Situated right next to the 90/94 expressway, only a mile from the CTA's blue line, and surrounded by several bus routes. It's tucked away behind a small apartment building on a residential street, so it's perfect for quiet nights in after spending the day exploring the city!

Guest favourite

Guest house

4.89 out of 5 average rating, 140 reviews

The Roscoe Village Guesthouse

The Guesthouse is located in a village within the city of Chicago. We are in the heart of Roscoe Village and walking distance to the CTA brown line train. We are less than 1 mile west of Wrigley Field and a 20 minute train ride to downtown Chicago. Right outside your door are restaurants, boutique shopping and cafe's. Plenty of free street parking around the house. I offer this unique & personal space to guests when I am away.

Guest favourite

Guest house

4.89 out of 5 average rating, 482 reviews

Coachhouse in central OP 4 blk to L

Just updated, furnished 1 BR 1 BA apt in Frank Lloyd Wright Historic District. Parking, kitchen, washer/dryer in unit, Air/Heat, Smart TV. Free wifi. Central location: 1 blk to farmers market, near Hemingway / Frank Lloyd Wright attractions. 4 blocks to green line. 20 min ride to downtown Chicago. Available for longer term stays.