Holiday rentals with breakfast in North Side

We stayed at Rachell and Cyd’s for about 3 months after relocating to the area. We absolutely loved the home as well as the walkable neighborhood, park, and downtown. We were made to feel at home with tons of useful items, abundant clean linens, and a cozy space. Cyd was very responsive at all times. This lovely house is a no-brainer for a comfortable stay on the North Shore. We will miss our time here.

FANTASTIC!! Great host! Awesome location! Clean house with everything needed available.. my kids loved the house, it felt like home away from home. Peaceful … Wish I could give more stars than 5!!!

My family and I rented Kevin's place for my niece's wedding. we enjoyed ourselves and the accommodations. Kevin was super responsive and made us feel welcome. the neighborhood is isolated but peaceful.

this was a great place lovely 😍 will book again and who ever reading this should book to

Perfect place to stay for our visit to Chicago with friends! There was ample room in the BnB for all of us, including a spacious dining and living room. The kitchen was very well stocked including coffee, juice, eggs, and toast for us to make our own breakfast (a welcome surprise!). It was very walkable to transit, with a CTA Blue Line station nearby. Thatheu was very responsive and check in was straightforward. Also the later check-out time was very convenient as we were able to take the time for breakfast before heading out for the day. Thanks again for helping us to have a great trip!

We had a wonderful experience staying at the Chic Cottage and would recommend it to any one looking for a comfortable home away from home place , available at a great price and good sub urban location with Super Markets and restaurants close by .

Had a great 2 night stay. Everything was clean and exactly as pictures and described. Very cute decor/theme. The layout was great for us, family with older teens. Lots of space and TVs. Great restaurants and some shopping within walking distance. Really good value. Walk to the beach and trails. We were in town for a nearby event and really enjoyed the area this place was in. Host was very responsive and answered questions beforehand. We had no issues with our stay at all and would absolutely recommend.

We rented this for a two night stay to attend a couple of Cubs games! You can’t beat the location!! Def go as early as you can before if it’s game day parking and getting through to the property was a beast because we arrived later than we planned.

Adam's place was very clean, comfortable, and well appointed. I appreciated the touches, the abundant parking in front, the proximity to the University of Chicago.

I enjoyed the apartment, it was very nice. It lived up to the pictures and description on the listing.

Chad and German were amazing hosts! Their place was perfect for our weekend. We planned a surprise birthday getaway for our son at Wrigley Field. It was so easy to get around with lots of restaurants within walking distance. It was also fun to have him blow out his birthday candles under the disco ball.

Carol’s place was very comfortable for our family of 4! Amenities were all as listed and everything was clean and inviting. We hope to stay here again the next time we visit family in Blue Island!

DW was very flexible and responsive. He was very accommodating to allow us to check in early and flexibility on check out as well. The location is good - if you are super sensitive to the noise of the train it may not be ideal, but the proximity to the train stop and Wicker Park was great. You must go to Mindy’s bakery - if I lived this close to a place like that I would gain so much weight 😅. Thanks again!

It was a nice place. Had everything needed. The locality is really good. Quiet, peaceful and nice people.

The house was comfortable and spacious

Great location nice view amazing host

You get exactly what you look for. The location is awesome and I found parking immediately. Great place

I recently had the pleasure of staying at Christiane's & Patrick’s beautiful home, and I can't recommend it highly enough! From the moment I arrived, I felt welcomed and at home. The space is impeccably clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. Both were outstanding host—responsive, friendly, and full of great local recommendations. They went above and beyond to ensure my stay was perfect, checking in to make sure I had everything I needed.

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

Mary's place was a great location for our short trip to Chicago! It was a short Uber drive from the airport, and a short drive to the All-State Arena. We did arrive late at night due to flight delays and opted for an Uber versus the train. I am glad we did cause it seems like the train station is under construction for the side we needed and would have been a bit more of a walk departing from the other side, but definitely not a dealbreaker or anything. The house is a short walk from this breakfast place that we actually went to twice during our short stay, with other options nearby. Overall, the house felt cozy and clean, but we did struggle with getting in the bathroom first thing in the morning with the other guests in the house during our stay. Mary was very responsive and a great host to us during our stay. The bed was comfortable as well and the room had amble space for a large suitcase, a carry-on, and two large bags with space to spare for two people.

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.

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!

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!

Great communication and a comfortable stay!