Family-friendly vacation rentals in Highland Park

Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.

Every year we visit Cypress there are more improves and amenities. Always a great stay and so much to do. Amanda and her team run this place like a well oiled machine. We visit once in the winter and once or twice in the summer. A favorite for sure.

Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!

This place was extremely great! It was close to downtown and lots of restaurants and food near by the bnb! Only thing I’ll say is the shower head is kind of flimsy but besides that everything is nice clean and the rooms are huge! Very peaceful and quiet over there!

The house was very centrally located and convenient to everything in Lake Geneva. It was a good size for my adult family to stay and we enjoyed the common areas for gathering. The house is old but in a way that we found quirky and charming, and overall clean and functional. There is only one shower but we didn't run out of hot water so it worked out. Parking and entry were very easy. Overall a great find and value if you are okay with an older place and want to prioritize a central location with several private bedrooms.

We really enjoyed our stay! My family came in from New Mexico for my daughter's wedding, and we drove in from Illinois. Unfortunately we didn't have time to enjoy the outdoor spaces, but the home was very comfortable. The garage provided a great "hang out" space. We set up bag boards and had a great time! 10 out of 10 would definitely recommend! This was my first experience staying at an Airbnb. Thankfully Will was very easy to work with and made it a positive experience.

Loved our stay. Cool neighborhood with lots to do in the direct area. Great advice from Kyle about where to go. Would definitely stay again!

Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!

Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!

These hosts are lovely as is this space. The amenities are wonderful and go beyond what they would need to provide - making travel easier! The apartment is spacious, comfy and clean. The area is full of places to go and also right on the Clark bus line, making access to the rest of the city easy peasy. Highly recommend.

This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!

Convenient location with lots of space

Definitely a great weekend! The look, and feel of the place was very comforting, and had a great flow. Design was tasteful, and anything that was needed was right where you’d expect it to be! A definite recommend!

This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.

This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.

Absolutely loved staying at Sylvia's! The camper is very conveniently located within the park - close to all the amenities and activities! Easy to access, beautiful grounds and a very peaceful stay for my family and I.

We had a fantastic time here! The property has an incredible deck that extends into the surrounding forest. We had breakfast outside every morning! If you love wildlife, you'll love this place.

Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!

Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

nice place, was represented well in the pictures. we went for Valentines weekend and enjoyed the fireplace. It snowed our first evening there but the association cleared the drive and sidewalks quickly. I can imagine this would be a summer location with proximity and closeness to Lake Como.

A great stay right near a Main Street. Tons of options for going out but still quiet in your space. Warning. You will smell the BBQ restaurant and you will salivating.