Guesthouse vacation rentals in North Side

Place was fantastic. Everything as advertised. Niles was a pleasure to deal with and even leaves some nice extras for you too. One of the most comfortable beds in any B&B I’ve stayed in. Perfect for business or pleasure. Five stars all the way. Definitely using again!! Parking too!!!!

We loved our stay! The space was so cute and cozy. It was also very clean with thoughtful touches throughout the space such as water in the fridge and snacks. Host was very responsive and helped us immediately when we needed assistance. I would definitely stay here again!

Mat is an amazing host. His property is incredible and he's extremely responsive. Would definitely recommend this airbnb!

Loved our stay at The Rectory! The location was great; walkable to DePaul and close to restaurants, shopping, DePaul and Lincoln Park Zoo. The unit looks exactly like the photos. Instructions were clear for check-in and check-out. Will definitely come back. We enjoyed our stay!

Very nice place and very comfortable. Only a block away from a street full of shops, restaurants and bus stops. It was also about a 10 minute walk to the blue line. Very quiet and secluded spot as it was behind the main house and had an alley behind it.

The Solar Victorian Coach House was perfect for my visit to Chicago! Access was easy and I felt safe. Owners, Joe and Shannon, were proactive with instructions and prompt with replies to my questions. The place is very comfortable with a great bed and bedding and very clean. It was well lit, and they offered local coffee along with a nice coffee maker. I felt at home, safe, and happy in their beautiful space. It was quiet and peaceful but also within walking distance to many coffee shops, restaurants and other shopping. Great hosts, great neighborhood and very welcoming place. I will be back soon and highly recommend!!

The location was perfect. Jury steps from Wheaton college. We stayed here during the Wheaton College Christmas Festival which we were able to walk to. Angel’s place was clean, had a Keurig with different choices, and filtered water. We had everything we needed for a short overnight stay. Thank you for a great stay!

thank you for the great place to rest

This was a perfect place to stay while my friends and I were attending alumni weekend at the University of Chicago. The Airbnb is very convenient to campus, and it was clean and comfortable and had plenty of space for relaxing and hanging out during downtime over the weekend. Daniel was a perfect host and was kind enough to allow us to store luggage for a few hours after check out. Highly recommend!

My family and I stayed at Casey and Esteve's place for 6 days. The hosts were responsive from the time of booking until the end of our stay. The location was great, 10-15 mins walk from public transportation which made Chicago downtown easily accessible. The house was clean and fully stocked with all the basic amenities plus some added bonus (coffee/creamer/sugar for the coffeemaker, toiletries, etc). The bed and pillows were very comfortable as well. My family and I will definitely stay again and would highly recommend this listing.

Due to a family emergency, I wasn't able to stay at Robin's place. However, Robin was very proactive, responsive, and prompt in communicating. Also, I know Evanston pretty well, and Robin's place is in a great area that is very walkable with lots to do within a short walk.

Emilia's place was a nice retreat for my 4 days of training in Chicago. The location was great, near the training and not that far from O'Hare. The place was very clean, all amenities that I needed, and I will plan on staying here my next trip to Chicago. Thanks Emilia!

I had to do a little teleworking on my trip and I was worried about how that would work out. Turns out it was easier to telework from Christina’s place than my own. It could not have gone smoother. I would absolutely stay here again!!

I recently stayed at this charming Airbnb, and it was an excellent experience from start to finish! The property is beautifully maintained, with a stylish interior that perfectly reflects the vibrant character of the neighborhood. The space was spotless and equipped with everything we needed for a comfortable stay, including a full-sized kitchen, cozy furnishings, and thoughtful touches like local guidebooks and snacks. The location is unbeatable. We loved being within walking distance of trendy cafes, restaurants, and unique shops. Public transportation was also conveniently close, making it easy to explore other parts of Chicago. Our host was outstanding—responsive, friendly, and eager to ensure we had a fantastic stay. They went above and beyond to provide recommendations tailored to our interests, which made our trip even more enjoyable.

By far the best place we’ve stayed in the Chicago area. So close to the airport, super easy check-in and check-out. The place was warm and quiet and had great towels and amenities. Couldn’t ask for more!

Adorable place. Very quiet neighborhood. Everything you could ask for in a rental.

This was a very nice place to stay. Would recommend. Highly responsive and kind hosts.

David and Jane were both super friendly and responsive when I reached out with a few questions during our weekend stay. The entry in the back of the apartment might have been confusing, but their instructions provided proactively were so helpful, we had no issues at all. The apartment was clean and all of the amenities were as-advertised. Definitely recommend this apartment - we would stay there again if we have a need to be back in the area.