Holiday rentals with a balcony in Cook County

We had a wonderful stay at the Craftsman Gallery. We were a group of 5 women and stayed 4 nights, celebrating a couple of birthdays. Matthew was very responsive and accommodating. We were able to follow the instructions to access the gallery no problem and the place was clean and ready. The place itself was just as described and was perfect for us. Access to the blue line couldn't have been closer and ubers had a safe place to pull up. Went to a few restaurants in the area and they were excellent (D'Agostino's right across the street and Windy City Cafe a block or so away). CVS and groceries/asian market super convenient as well. We had a very comfortable stay and would stay here again. City sounds (referenced in other reviews) were not a bother to us. Check out was a breeze. Would stay here again!

This is a nice and convenient apartment to stay in for families visiting the local area. Garden apartment means there is not a lot of sun light as it is ground floor. Street parking a bit challenging because it was a graduation weekend but they do have larger lots within moderate walking distance. But regardless - this apartment met our needs. Nice walking neighborhood and found nice local restaurants. Close to DePaul.

Daniel’s place is in the heart of Pilsen, and very close to Downtown, Hyde Park etc, with lots of public transport around. The place is spacious with a nice back facing balcony. Daniel was very communicative, and very kindly allowed us an early check in as we had a lot of luggage. Would highly recommend his place to anyone visiting Chicago!

Convenient spot right on the train and good bus access around the city. Grocery store a few blocks away and tons of good restaurants and bars within 15 min walk.

Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location

Appreciate the great communication and beautiful accommodations, perfect for our multigenerational group. Would definitely come back and everyone in my family felt the same way.

This place is great for large parties. It’s close to bars, restaurants and the main strip of Lincoln Park. Being close to the hub of things means it’s a bit noisier. Not crazy or anything, but if you’re not use to city noise this can be surprising. The bedrooms are laid in a way that not every room is private (glass doors), shared spaces, etc. more of a heads up when you enter into the unit there’s a flight of stairs to get to the unit. Not a deal breaker, but we had someone in a walker which made it a bit more challenging. Would rent this space again!

Linda was a truly gracious hostess and immediately responded any time we had a question. I can highly recommend her beautiful home!

Liz was a wonderful host. Informative and detailed. She has literally thought of everything you would need for the stay and then some! Fully stocked cleaning supplies, toilet paper, linens and kitchen items. Very clean and neat place that allowed for everyone to have a space of their own and not feel cluttered. Thank you for such a wonderful experience.

The Roscoe house was the perfect spot for our trip with our teenage daughter and her two friends. The location had everything we needed and could ask for in terms of nearby, fun and food, as well as close to everything we wanted to do. And the place itself was stocked better than any place we’ve ever stayed, which made cooking and hanging out easy and fun. And it felt like a home away from home. But elevated since the decor and the layout we’re super cool and modern and unique. We definitely will stay here again. It made for a wonderful trip.

Had a great stay over St. Patrick’s day weekend. The apartments are in a very walkable area with great access to public transportation. Fenton was also very quick to communicate and gave clear instructions. 10/10 would recommend to anyone.

We had a large family in town for a wedding. The number one concern when searching was if we'd be and feel safe. I must say that the neighborhood was quiet and family friendly. People were out walking their dogs and smiling in the morning and it was quiet at night. There were quite a few shops and restaurants within walking distance. I would definitely book again if in the area.

Great place and stay! Location is amazing!

Really nice home in a great location. Everything checked out. The only thing you need to worry about is that there’s just one restroom in the house. Apart from that everything was great!

Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!

Sometimes pictures don't tell the whole story. In this case, the photos of Matt's property didn't do the property justice! This is a gorgeous, beautifully appointed house - difficult to fully convey in photos. Absolutely stunning! From the living areas to the dining room to the kitchen to the bedrooms, it was all perfection - welcoming, clean and user-friendly. The house is located in a wonderful area - restaurants and bars easily within walking distance. Despite the busy-ness of the surrounding area, the house itself was blissfully quiet (a rare find in the heart of Chicago)! Matt was super responsive to the few questions I had - a wonderful host all around. 10/10 would recommend this house, and I can't wait for my next stay!

Highly recommend this stay if the area is your prime spot. The location was 5-20 minute walks of a huge range of restaurants. We didn’t mind the 20 minute walk to Ukraine Tryzub Kitchen, we split it up with a nice spot half way through. Beds were very comfortable and it was a cozy space. Loved the blackout curtains with the sun rising so early and needing to sleep in with taking time off work. It’s a great central location and a perfect spot. Great stay

We enjoyed our stay! First and foremost Colin was superb! Very responsive and respectful. Many pros about the place: loved the bright bedroom, walkable to many restaurants, neighborhood felt safe, we did not travel with young kids but kids bedroom could have been fun for young kids, the parking spot provided was a huge plus. cons were loud AC, mattress was not as comfortable as one would hope. Place could use some simple aesthetic up keep. Overall, we enjoyed our star and felt very comfortable! Thank you Colin for being above and beyond host :)

Tom’s place was exactly what we needed for a weekend in Wicker Park! The location was perfect to enjoy restaurants and stores, and the ease of access with the keypad was great for check-in and coming/going. The unit was very clean and spacious, and having a dedicated parking spot was amazing! Would definitely stay here again.

We had a great time staying at Matt and Christy’s place. The neighborhood was quiet, providing space to rest after busy days. The apartment had a lot of charm and was a comforting place to return to. It took us about fourteen minutes to walk to the closest metro station, but overall was centrally located for our purposes. The hosts are helpful and were quick to respond when we needed additional supplies.

We loved this place! The vibe is amazing, the neighborhood is safe, and transportation is super close. The host is friendly and helpful…we would definitely stay here again.

the location you can't beat if you are coming to town for a Cubs game. Just down the street from Murphys Bleachers, a great rooftop where you can listen to the game, and lots of space within the place. when we didn't have the corrects sheets for the Murphy bed Kimberly sent them over as soon as she could. I'd stay here again.

Our stay could not have been better. We enjoyed all the gathering spots the house afforded — especially the outdoor dining area and the back deck seating area. We had the best time!

This condo worked great for our family of 5 (3 teenagers). The location was ideal to the train and bus stops. We were able to easily walk to Old Town where we enjoyed Second City, Corcoran’s Pub and Jeni’s Ice Cream. We felt the condo was in a safe location. You can hear the L go by, but we didn’t mind it; reminded me we were in the city. We were able to secure a parking spot (SpotHero) right behind the condo which was ideal. Was it a bit pricey, yes…it’s Chicago, everything was expensive. Enjoyed our visit!