
Bed and breakfast holiday rentals in South Side
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Top-rated bed and breakfast rentals in South Side
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness and more.

House 5863 Bed and Breakfast Room 2
Room 2 Features: Queen bed Private bath [Bath is located across the hall from the guest room] Flat-screen television w/ free cable Wireless internet Ceiling Fan Alarm clock Bathrobes All Rooms include Central Heat/ Air Conditioning This room offers quiet comfort and value. We have discounted the price only because the bath, although private, is located across the hall from the guest room. The room is located at the center of the house and is very quiet. * 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

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

Bright Room with a Garden View
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. Shares bathroom with 2 rooms Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Private Guest Suite • Sleeps 4 • Separate Entrance
⭐ Private walkout entrance ⭐ 1000 sq ft private guest suite ⭐ Fenced backyard + patio + fire pit ⭐ Pet friendly ⭐ Free driveway parking Welcome to beautiful Lake Zurich! This 1000 sqft walkout awaits you. The fenced yard makes it a pleasure to welcome your furry family members too. Whether you are here for an adventure or business, a couple, family, or a group of friends -please enjoy your stay! ✨ Our space is best suited for guests looking for a comfortable, quiet, and relaxing stay!

Top location, sunny UofC Prof on campus home
NO closer accommodation to the U of c campus, large wrap around deck with garden and small semi private deck. convenient access to lakefront, Obama house, Science and Industry museum, public transport. Excellent do it yourself morning breakfast in large kitchen, sparkling clean home. Newly renovated room, marble bathroom floors. More like a traditional bed and breakfast than airbnb. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

Historic campus house owned by U of C Prof
There is absolutely no accommodation closer to the University of Chicago and U of C. This spacious room is in an elegant, renovated old mansion. All rooms are scrupulously clean. Amenities include private en suite marble bathroom, underfloor bathroom floor heating, spacious closet and drawers, ironing board, hairdryer, comfortable leather reading chair and footstool and work desk. See all five rooms available in our lovely bed and breakfast here:https://airbnb.com/users/143937691/listings

(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.) A lovely and spacious bedroom in our home. 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. Meaningful conversation (if you want it).

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

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, and balcony.

SuperHost with Private bedroom/bath/entry Lakeview
Fun, vibrant residential neighborhood surrounded by bars, theaters, coffee shops, restaurants and boutiques. Private access to a one bed/bath with additional access to the 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."

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.

Spacious King Room in Boutique Wicker Park B&B
Spacious, bright and modern guest room located is just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Damen King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood.
Popular amenities for bed & breakfast rentals in South Side
Family-friendly bed & breakfast rentals

Historic campus house owned by U of C Prof

Private bedroom with shared bath

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

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

SuperHost with Private bedroom/bath/entry Lakeview

Caesar's Lair
Bed and breakfast rentals with breakfast

Romantic Queen Room in Boutique Wicker Park B&B

Historic campus U of C Prof. mansion, top location

Sun-Filled King Room in Boutique Wicker Park B&B

Large private room w/ shared bathroom in Boystown!

Queen Room w/ Balcony in Boutique Wicker Park B&B

Romantic King Room in Boutique Wicker Park B&B

Luxurious King Room in Boutique Wicker Park B&B

Cozy Garden Room in the middle of Boystown!
Other bed and breakfast holiday rentals

Historic campus house owned by U of C Prof

Private bedroom with shared bath

Great Edgewater/Andersonville private suite

Urban Oasis Pilsen - guest room in townhouse

Lovely UofC Prof mansion great on campus location

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

SuperHost with Private bedroom/bath/entry Lakeview

Caesar's Lair
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