Guesthouse vacation rentals in Cook County

Coach House Art Studio 2BR, By Northwestern

Escape to the charming Coach House Art Studio nestled in Evanston, just steps from downtown and Northwestern. This bright and creative space blends contemporary vibes and cozy comforts. Whether you’re here for work, university, or a relaxing getaway, enjoy easy access to restaurants, transit, and the lake. Come stay where art meets home. New 55” smart TV added to the living room w/ multiple streaming services and an in unit washer and dryer. Registration #: STR011 Date of Issuance: 05/20/2025

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Charming Guest House in Evanston

Welcome to a one-of-a-kind stay in Evanston — a charming Coach House designed for guests who appreciate quality craftsmanship. Just a 10-min walk from Lake Michigan, 10-min drive to Northwestern and Loyola Universities, and steps from public transportation. The spacious loft bedroom, with its natural light and tree-lined views, offers two comfortable beds in a serene setting. Ideal for visiting academics, professionals, or design-minded travelers, this Coach House offers an elevated experience.

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

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.

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

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!

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. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

Cozy Guesthouse near NU - next to Lee Street Beach

Welcome to our cozy and comfortable guesthouse nestled on a quiet and beautiful neighborhood in Southeast Evanston. We are 2 blocks from Lee street beach and 10 minutes walking distance to the Main Street El train (purple line) and Metra stop. We are a 10 minute walk to downtown Evanston and Northwestern University. We are 10 miles from downtown Chicago.

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.

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.