Bed and breakfast holiday rentals in Cook County

Find and book unique bed & breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in Cook County

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness and more.

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Private room

4.82 out of 5 average rating, 28 reviews

House 5863 Bed and Breakfast Room 1

Room 1 Features: King bed In-suite bath Flat-screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bathrobes All Rooms include Central Heat/ Air Conditioning This is the owner's favorite room as it has a large bay window that overlooks the park across the street from the bed & breakfast. The room is adjacent to the common living area. * All guests must be fully vaccinated for Covid-19 and at least 2 weeks after 2nd shot. * City of Chicago Bed and Breakfast License Number #2207267

Guest favourite

Private room

4.99 out of 5 average rating, 108 reviews

Lovely UofC Prof mansion great on campus location

No closer accommodation to U of C anywhere. Large light filled bedrooms, private bathrooms, huge balcony in 4 story light filled home on sought after University of Chicago campus. Two blocks from the University, four blocks from Lab school. Short walk to train to downtown, beach, bike path, Science and Industry Museum and lakefront. A rare, privately owned home in the heart of campus. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Guest favourite

Private room

4.94 out of 5 average rating, 248 reviews

(BR#1) Welcoming, warm & comfortable, 3 guests

Welcoming, warm & comfortable home, BR#1 for up to 3 guests. (LISTING #1 OF 3; see other listings for additional space.) Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).

Private room

4.68 out of 5 average rating, 81 reviews

Huge (2Beds) 1 Bedroom

Enjoy the glamour of this stylish, upscale place. 2 Beds (Queen+Full) in this bedroom. You’ll love the stylish decor of this charming place to stay. Working / computer table with walking closet. Free Breakfast and Wi-Fi. Just 1.5-2 miles from Downtown Evanston and Northwestern University, you are a straight shot from countless dining, shopping, & entertainment options. Close to Downtown Chicago. Bus station is walking distance which connects you all around Chicago. Beaches are about 3.5 miles

Guest favourite

Barn

5 out of 5 average rating, 156 reviews

The Good Farm: Barn BnB on 44 acres near Lake Mich

Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully stocked barn apartment with gorgeous views! You'll be near Indiana Dunes National Park, tree-lined hiking/biking trails, wineries, cafes, outlet malls, & antique shops. Roast s'mores in the fire pit, watch chickens free range through the yard or grab a bite to eat downtown Valpo/Chesterton/MC—the perfect getaway for families or friends who want to relax or adventure in nature.

Guest favourite

Private room

5 out of 5 average rating, 108 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

Guest favourite

Private room

4.95 out of 5 average rating, 250 reviews

Great Edgewater/Andersonville private suite

1904 Greystone 2-Flat gut rehabbed into Single Family Home: Loft style w/ exposed brick & duct work. Private guest suite (w/ separate entrance) that sleeps 2-4 persons, There is a King bed in the private bedroom & queen tempurpedic topped sofa sleeper in the private living area, wet bar w/ mini fridge, Keurig coffee maker, sink and microwave, 2 flat screens TVs, private bath, piano, and use of the backyard garden. Also, the main house Kitchen/Living Rm are available to use upon request

Private room

4.64 out of 5 average rating, 66 reviews

Comfy room in northside Chicago B&B

Located a two minute walk from the Belmont el station, this room sleeps two, on a full size bed. Furnished with nightstand, dresser, chair, TV. Guests have private use of the full bathroom with tub just across the hall. This room is on the first floor, adjacent to our main sitting room and kitchen. Wifi, continental breakfast, and $10 off at the neighboring Trader Todd's given to all guest. All check in is self checkin. Guest must provide ID, credit card and signature to check in.

Private room

4.86 out of 5 average rating, 353 reviews

Large private room w/ shared bathroom in Boystown!

Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Private room

4.8 out of 5 average rating, 172 reviews

#7 Historic Chicago Home - Bunk Bedroom(Twin&Full)

The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan - perfect for gatherings of any kind. We're in the heart of the Rogers Park, walking distance from many restaurants & shops, one block from Loyola Beach Park, and 5-15 mins walk to 2 different train / metro lines. The home is run by friendly local folks who are happy to help during your stay.

Guest favourite

Private room

4.9 out of 5 average rating, 345 reviews

SuperHost with Private bedroom/bath/entry Lakeview

Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access, use of entire level including bright spacious family room. Located minutes from bus, DIVVY bikes, and "el" (2 blocks), Wrigley Field (6 blocks) and 1.5 miles to Lake Michigan. Walk Approximately 20 minutes by train to the downtown area or central city "Loop."

Superhost

Private room

4.89 out of 5 average rating, 19 reviews

Villa Dubois Guest House Room 1

Villa Dubois Guest House is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe, just minutes away from local restaurants, downtown, public transit (both bus and train), Divvy Bike Stations, and McCormick Convention Center. Room 1 is a private room with shared bathroom for up to 2 guests. It is one of our largest and brightest room.