Bed and breakfast holiday rentals in South Side

Great location, great accomodations, and most importantly amazing hosts! Tripp and Todd were so welcoming, I felt right at home. They provided helpful suggestions for meals, activities, transport, etc. Hosts were in communication from the moment I landed to coordinate checkin, and allowed me to drop off my bags early when I arrived prior to the check in time. The location is great, only a few minutes walk to Clark Street which is well populated and has many restaurants and independent shops. Do yourself a favor and book with Tripp and Todd if you ever find yourself in Andersonville/Edgewater!

My adult daughters had a lovely stay in your home. Your breakfasts got rave reviews. Your spot was the perfect location for them to attend the graduation and events at Northwestern. Thank you for opening up your home and being such friendly and helpful hosts!

I always enjoy stays at the Hamlin House and this was no exception! The Blue Room is lovely, - spacious with gorgeous windows and a spa-like bathroom. Wish I could have stayed longer!

We felt warmly welcomed to Patricia’s home from the moment we arrived. The bedroom and bathroom were comfortable and the breakfast was amazing! A special breakfast was even prepared to accommodate a food allergy! Lovely visit at breakfast on the outdoor deck, we would stay at Patricia’s again!!

Everything was perfect! Enjoyed the room and breakfast. Staff was very friendly and helpful.

Caryl was very responsive. I had a small issue with my door code and she fixed it quickly. The room was very big and comfortable. The lovely breakfast was a nice surprise. Perfect location if you need to be near UChicago. Felt very safe. Would stay there again.

Caryl was a wonderful host who went above and beyond to make sure I was comfortable. My room had everything I needed, and the house is a convenient walk to UChicago. I will definitely be staying here again on future visits!

A lovely room, clean and cozy, in a great location. Very walkable! My room was first floor street-facing and I didn’t notice any outdoor noise (expect a little rumble from the train). Laura was incredibly responsive and helpful. I’d stay here again. I didn’t want to pay for parking, and I’m familiar with the neighborhood, so I chose to park several blocks away.

It was a wonderful stay with a very hospitable host. We loved the access to the beautiful kitchen with instant hot water for tea. The homemade baked goods were a delicious treat in the morning. The room was immaculate. The back rooms face the tracks for the busy Chicago Transit Blue Line, so if noise bothers you, ask for a room facing the street.

Very cozy place in a calm tucked away neighborhood. Would definitely stay again!

Loved the king sized bed, and the large shower. Location was perfect. We stayed in the Wolcott which is on the front ground floor. Has a beautiful brick fireplace in front of the bed. I think this building had about 6 units. Everyone was friendly. They provided a community kitchen and breakfast was nice. Bagels, muffins, pastry, boiled eggs, oatmeal, coffee &tea, and juice was all very fresh. Easy in, easy out! We’ll return soon! Thanks!!

Nidhi’s place was exactly as described. I can’t say enough good things about it. The bed was very comfortable. The Jacuzzi and mood lighting was fun. The dorm size fridge and microwave wow you don’t normally see that in a motel anymore. Everything was clean and the water pressure was very good. Plenty of hot water.. I was shocked that every morning a full complete breakfast was in the lobby for free not to mention 24 hour coffee! We were there on a business trip and across the street were excellent restaurants, including an upscale bar with delicious meals, a sushi house, Chinese restaurant and a diner. You could also get your nails done and book a massage right across the street. I enjoyed taking the train into Chicago. It was very simple to buy your ticket on the spot not far from the motel at the station. The neighborhoods surrounding her place were beautiful. I did a lot of walking and there were sidewalks everywhere making it safe. She and the check-in managers we’re friendly.

She was very polite and helpful. She didn’t mind letting us back in late at night. I would definitely stay here again

Great on all fronts. Lovely hosts, exceptionally clean room, great food, can't say enough positive things. Looking forward to staying here again sometime.

Phenomenal stay. Zero notes. Hands down one of the best I’ve been

I was in Chicago for the night, and this stay made me feel right at home! We had a BEAUTIFUL room, and all the shared spaces were spotless and well-designed. I will definitely come back to Chicago and book this unit again. Most comfortable mattress I've ever slept on as well.