
Kid-friendly vacation rentals in Chesterton
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Top-rated kid-friendly rentals in Chesterton
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Popular amenities for Chesterton kid-friendly rentals
Kid-friendly house rentals

Vacation home on south end of Cedar Lake
For our trip this home was perfect. It was near the friends we were visiting, short drive to Lake Michigan, great restaurants in the area, and we loved having a kitchen so we could grab some groceries and save some money on meals. The home is older but so is ours so we felt right at home. Everything was clean as well. We hope to stay here again.

Beautiful home with Beach views in Beachwalk
Well-maintained house, spotless upon arrival, great view of the area from the kitchen. Ice machine was a great touch especially with a bunch of people in the house! Would definitely come back!

5 Bedroom Luxury Home In Heart of Beachwalk Resort
We all walked in and said WOW! It was beautiful and had so much charm. We have stayed in many rentals and this was by far the cleanest and most organized. We traveled with 3 couples and there was plenty of room to gather and socialize and room to just chill by yourself. The boardwalk made for a wonderful morning walk. Brittany was a terrific host answering any questions I had and providing a list of thing to do in the area. Certainly worth the money! We would definitely stay again. Rita

Beautifully eclectic Sawyer cottage
Really enjoyed Tim's place. It was very spacious and clean and the space had a great vibe. It was centrally located to a lot of restaurants and places and the hot tub was huge. Nice quiet location. Would definitely stay here again.

Roomy and Private Getaway for Families & Friends
Very spacious and just as described. Perfect location for visiting family and would be great in the summer!

Riverfront Oasis: Parks+ Kayaks+Relaxation Await!
Magical place!!! Beautiful community! We just loved staying in the River here with our dog! Rhiannon was the best hostess. This place is stocked to the nines with linens dishes, bowls, pots, pans. You name it! We were able to enjoy the river and. The park is right next door so it was perfect walking my dog! The perennial blooms were making a show when we were here so again. Just a magical place! We will be back for sure. Thank you so much to the Ford's for doing it right!!!!

Pet Friendly Perfect Spring Getaway with Hot Tub!
Great place and as the description suggests, it’s pup friendly! We lacked nothing during our time there and would highly recommend.

Cheerful 3BR 2BA Country Cottage Near Attractions
The place was exactly as described, loved it was pet friendly so we could bring Ivy with us. Nice fenced backyard, we even had a fire one night. Plenty of room for us and very clean. Would definitely stay here again.
Kid-friendly apartment rentals

Clean, spacious, walk to Wrigley! Self check-in!
We loved our stay. Amy was an excellent communicator. The space was clean, open and very inviting. I loved the location. I would definitely stay there again!

The Biddle House (#1)
We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

Archways at the Lincoln Park Zoo 2bed/2ba
Jessica’s place was great and perfect jumping off point for my family attending my brother’s wedding and other festivities.

Great Living
The accommodation is nice. It is clean, and the space is cosy and well kept. Catch the sunset from the sitting rooms, they are beautiful.

Garden Apartment in captivating Hyde Park
Nice location with nearby supermarket, cafes and restaurants. The nearby busstop to go downtown is also very nice and near. Great apartment with all the necessary amenities for short stay. 😁

Lovely 2 bedroom just a few blocks from the square
Have stayed here multiple times. Love it and will continue to come back!

Bridgeport Garden Apartment
Such a wonderful stay in Bridgeport!! Thanks to Juan and Nelly for their hospitality and personal touches around the unit. They went above and beyond to make us feel at home. It was a great location with plenty of restaurants within walking distance. We will be back for sure!!

Modern 2BRD apartment| 5min to McCormick Place
Clean and modern! Me and my kiddos really enjoyed our stay and I loved that there was plenty of free street parking. Asta and Andrew were incredibly responsive and were gracious enough to let us check in 90 minutes early. Thank you for a great stay!
Kid-friendly condo rentals

Entire 3Bed/2Bath Condo Near McCormick & Metro
We enjoyed our stay. John works hard to offer the best experience to his guests. The place was super clean and welcoming. Photos are matching. Close to everything with UBER. Some restaurants are located in the block. I recommend this appartement.

Convenient & Spacious 3BR Condo w/Free Parking
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

Dream Condo steps from Wrigley Field!
I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.

Marina Condo near Lake Michigan
Dave made us feel right at home and answered any questions we had. His place is near restaurants and stores which were very convenient! It is also a 12 minute drive to the national park and there are so many places to check out. It’s about a 45 minute drive to Chicago and there’s a train nearby if you want to take that instead into the city. I highly recommend staying here Dave’s place was clean and he was an amazing host!

Luxurious River North 3BR/2BA- Free Onsite Parking
Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown
Very great for a large group.

Gamers Getaway 20 minutes from downtown
Loved The Space! Everything Was Perfect! Any Problems Or Any Questions Daniel Was Very Helpful! THANK YOU DANIEL

Lincoln Park 2bed/2bath in Historic Neighborhood
This was our favorite spot in Chicago thus far! The location was amazing, so close to everything! My 7 y/o is obsessed with the Sears Tower and was thrilled we could see it from our window! :) The place was clean and beds were super comfy. Would totally stay there again! Thank you, Michael!
Quick stats about vacation rentals that are kid-friendly in Chesterton
Total rentals
20 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- University of Notre Dame
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Museum of Science and Industry
- The Field Museum
- Wicker Park
- Chicago History Museum
- Willis Tower
- Potato Creek State Park
- Flossmoor Golf Club
- Brookfield Zoo
- Lincoln Park
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point
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