Pet-friendly holiday rentals in Woodlawn, Chicago

This was a fantastic stay! The space was beautiful, spacious, clean, and well located. Definitely a great option if you're in the area and need a larger space.

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

House is centrally located . Clean. Host was responsive. 100% recommend this property !

Michael was a great host. Very responsive and friendly. The property was exactly as described. Very clean and looked just like the photos

We stayed for almost a week with three dogs. Sarah's place was perfect for our needs - great backyard, comfortable beds, clean and equipped kitchen, and awesome location - close to Chicago, Indiana dunes and easy to navigate thru, no traffic. Sarah and her family (and their amazing dog Chandler) are super friendly and helpful. We will definitely stay there again once back in the area.

We had a wonderful stay at this Airbnb in Chicago! The space was incredibly clean, cozy, and felt just like home. The location was perfect—just a short walk to the zoo and only a 10–15 minute drive to downtown, which made getting around super easy. The neighborhood was safe and peaceful, perfect for relaxing after a day out in the city. The hosts were fantastic—very responsive and accommodating, always available to answer any questions we had. Would absolutely stay here again and highly recommend to anyone visiting Chicago!

Overall great for our stay, Fairly close to a lot of things.

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Excellent place to stay, easy access to highway, quick ride to downtown

This was a perfect stay for an amazing weekend getaway and Festival experience. The area was walkable and had several great options for food and bev. Free street parking directly in front of the property, secure garden level access, and all the instructions and guidance were well laid out. Additionally, they had a guidebook that was well put together and everything was cohesive and exactly as pictured and described in the app. John was very responsive, friendly, and he and his family provided a perfectly appointed environment for our getaway… And their dog, Star 🐶 was such an angel! We had a great time, thank you!

The place was spectacular. The views are breathtaking. My family and I loved the place.

Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

⭐️⭐️⭐️⭐️⭐️ An unforgettable stay in the heart of the city! This Airbnb was absolutely amazing! The location couldn’t have been more perfect right in the middle of everything, with easy access to restaurants, shops, and public transportation. The space was spotless, beautifully decorated, and felt like a true home away from home. Our host went above and beyond to make sure we had everything we needed. Their hospitality, local tips, and quick communication made our stay even more enjoyable. You can tell they genuinely care about their guests’ experience. If you’re looking for a comfortable, stylish place to stay with an incredible host in Chicago, look no further. We’re already planning our next trip back!✨

Great getaway place to stay at. Beautiful patio area as well!

My family of 5 including my elderly parents had a lovely stay at Rachel and David’s house for our son’s graduation from UChicago. It is in a quiet location that is very close to the university. The hosts were very friendly and flexible. The place is spacious, light and airy and extremely clean. The beds (especially the two large bedrooms upstairs) had usually comfortable beds. All in all it a 10 out of 10!

The hosts’ of this property were great and accommodating. They catered to our altered schedule and compromised on a request of ours. We will definitely stay here again.

Terrific apartment, and spotlessly clean. We were only 2 people, but it had a king and a queensize bed in 2 separate bedrooms, as well as a comfortable and well dfurnished iving room. Very modern and up to date.. Kitchen was ample and well equipped and stocked with basic staples. We didn't meet our josts ut they were responsive to our messages.

Un lugar bonito. Está algo alejado del centro pero si rentas un auto, está excelente para poder moverse. Los espacios son muy adecuados y limpios.

Five star stay all around. Great location, near a nature reserve. Large living room and bedroom, lots of amenities. Cornell supplied excellent directions and instructions. Super easy to communicate with. Thoroughly enjoy the stay. Would love to book again, but calendar is full and I know why - this please is great, Thank you Cornell!

this is our second time at James place. it was great the first time and great the second time. The apartment is comfortable, inviting , spacious and has all you need for the stay. Bathrooms are clean. Kitchen is well equiped. access is easy. Parking on street is easy. Grocery is nearby. it is pretty close to uchicago campus so it is perfect isf you are visiting that area. James is a very responsive host. I hope it is a available when we visit our daughter next!! I would take it again!!

Lovely apartment, perfect for the 4 of us. Kitchen is wonderful and well stocked, beds are comfortable, and bathroom was clean and had everything we needed. Just a 5 minute walk to the Metra train station or bus stops that will take you anywhere you would want to go. Would stay again and do recommend!

Very nice space and Eric was very responsible when we had questions.