Search South Side Bed & Breakfast

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured B&B in South Side

"4th time staying and enjoy everything as advertised "

includes taxes & fees

23 Feb - 24 Feb

"Was having surgery but was canceled so I didn’t get to stay very long but would definitely stay again"

includes taxes & fees

25 Feb - 26 Feb

"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"

includes taxes & fees

25 Feb - 26 Feb

"Was surprisingly excellent "

includes taxes & fees

27 Feb - 28 Feb

"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "

includes taxes & fees

24 Feb - 25 Feb

"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."

includes taxes & fees

24 Feb - 25 Feb

"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"

includes taxes & fees

11 Mar - 12 Mar

"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "

includes taxes & fees

24 Feb - 25 Feb

"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."

includes taxes & fees

24 Feb - 25 Feb

"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."

includes taxes & fees

24 Feb - 25 Feb

Fridge, microwave, coffee/tea maker, toaster

"The property was clean and attractive. It’s located in downtown Homewood with an easy walking distance of restaurants and shopping. The door takes a little bit of time to figure out. You need to wait time before you can hear it lock. Some of the door knobs were coming loose. A few of the ceiling fixtures were coming loose as well. It was a safe, clean, convenient, affordable option. I appreciated that the host answered my questions right away. Guest should know that there is parking available in...