
Kid-friendly vacation rentals in Chesterton
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Chesterton
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton kid-friendly rentals
Kid-friendly house rentals

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home
Great house for the value! Clean and lots of amenities! Wish we visited in summer as fenced backyard is great! Stairs to second floor are steep but in good condition with handrail! There are local trains that are present throughout the day/night, but their sound didn’t bother us 😊 Overall a great value and lovely vintage home! Host was very responsive and friendly! Thank you!

Serene Retreat in Beauty Creek
This Airbnb was such a peaceful escape beautifully put together with so much intention. The overall vibe was serene and calming, which was exactly what I needed. One of my favorite parts was the screened-in porch perfect for enjoying the fresh air without worrying about bugs. I also really appreciated the sound machines in every room; it was such a thoughtful touch that made sleeping even more restful. If you're looking for a stay that brings peace and comfort, this is the place. Highly recommend!

National Park Nature Lover's Paradise
This location was clean, quiet and comfortable. Perfect spot for enjoying the Dunes, hiking and birdwatching. I own a non-Tesla electric vehicle and there was a reliable set of chargers (6) at the Meijer store 5 miles away.

The Lake Escape - 5 Mins from beach, casino, & zoo
We really enjoyed our stay! the place was nice, spacious and well equipped.

Pool House near the Indiana Dunes
The location was so peaceful and close to everything (10 mins from the dunes). The house was comfy and had everything you could possibly need. Melissa thought of everything! The pool.. OMG the best! The heater made the water PERFECT! Made it even more special that we could bring our dogs. The fully fenced yard was perfect. Will definitely be coming back.

Welcome Home
Great place to stay while we were visiting our grandchildren for the weekend! It was nice to have the kitchen to make coffee and breakfast in the morning. Comfortable bed and private, quiet location. Thanks again!

Newly Renovated with Finished Basement
Hello the stay was GREAT and the house was very nice , I would definitely recommend a stay at the bnb ! I would also rent again ! Thank you for having us

Cozy House near Beach, Casino, Outlets, & Hiking
This was such a cute, cozy, and clean place to stay for a weekend trip! The house provided everything we did need and anything we could have needed. Hosts went above an beyond to make sure we were welcomed, including a personal note and bottle of wine, and they checked in to ensure everything met our expectations. Location were close to all attractions and was in a nice neighborhood. I would definitely stay here again!
Kid-friendly apartment rentals

Plant MOOD FREE Wi-fi, parking, washer & dryer!
We really enjoyed our stay. The place was very clean and welcoming. The bathroom had a nice shower with good water pressure. The bed was comfortable and provided a restful sleep. Any questions I had, Siobhan responded very quickly and pleasantly. We went to a beer festival in nearby Munster and this was a great location to stay in.

Cute 1 bedroom apt near all MC has to offer
This was the perfect weekend stay. The apartment was clean and comfortable. Shopping and eating is all within walking distance. Definitely visit the Washington park zoo!

Private Entrance Guest Suite on the River
Great place. I wish I would have gotten there at check-in time, so I could have enjoyed the river more!

Miller Beach Retreat
Irene and Martin were very helpful and friendly. The place was cute and clean. It was exactly what I needed, peace and relaxation. The beach was a three minute walk and it wasn’t crowded. We brought firewood and outside by the fire pit there’s nice furniture and it feels like you’re in a little woodland area with nobody around.

Downtown Apartment on Lincolnway
The location, space, and comfort of the unit was perfect for our stay in Valpo. You can walk to so many restaurants and local attractions! The place is well stocked with the essentials and the decor is so wonderfully done, which made us feel comfortable immediately. Highly recommend a stay!

Cozy 1 bed, 2nd floor with private bath & kitchen.
Great little place which had everything we needed on a one night stop off on a road trip. Theresa was helpful and communicative

Charming apartment in Arts District
Such a perfect place for a fun quick getaway close to Indiana dunes state park and Washington park beach. Walkable to restaurants, coffee shops, outlet mall and farmers market.

Tiny Retro Studio for One Person
I loved staying at this cosy apartment. All Maggie's instructions were easy to follow and her place is very comfortable and well-appointed. The neighbourhood is quiet and a short walk to downtown. Thanks Maggie!
Kid-friendly condo rentals

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
We loved our stay at Danny's place! This was our first time visiting Lincoln Park, and the location of the home was perfect. We walked to restaurants, the Lincoln Park Zoo, and the beach. We appreciated being able to have our dogs with us and found the area very dog-friendly on our walks. Danny was kind and thoughtful with all the extra touches and responsive communication. He even caught us in person to make sure we had everything we needed. Our family felt safe walking in the neighborhood day and night. We even took the bus to downtown Chicago, which is only a few miles away. The house itself was very clean and large - our family of 4 plus 2 dogs had plenty of room to spread out and feel comfortable. We highly recommend the home to others and hope we can return again someday!

A Stones Throw from U Chicago South Campus!
It was a very cozy apartment with a nice set up. Easy access to university of Chicago and the lakefront trail. We really enjoyed our stay!

Urban Oasis | Great for Families w/ Kids
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

Ultra clean/cozy condo, 10 mins south of Downtown!
Great host and great stay! Beautiful home. Thank you so much!

Modern Hyde Park Getaway | UChicago
The apartment was clean and spatious, better than in the pictures. It's located in a corner of Hyde Park, at a 15 minute walking distance from the University of Chicago. It is a very residential area, with not many shops or restaurants near by, but if you walk 15 minutes east you will find bars, grocery stores and a few restaurants. I came to do research in the library's archive so it was very convenient. I had some problems with the door code sequence, but Erika was very helpful and responsive. My only suggestion is that more detailed information about the check in is provided, because not everbody is familiarized with lockers and codes! But my general impression was very positive! I'd definitely stay there again.

Marina Condo near Lake Michigan
Met our needs very well. There was a little restaurant on the premesis.

Unique Lincoln Park Duplex Apt
We had a great stay! The location was beautiful and prime - super walkable and lots to do in the area. The place was the perfect size for two and the apartment was super clean. Fireplace was such a nice touch! Check out was super easy and Bozena was super responsive. Would definitely stay again!

Chic boutique hotel near the beach & breweries
This is our second time staying in this home! We loved it so much the first time that we came back. Nicole’s home is very clean, in such a lovely part of town, and extremely cozy! We highly recommend!
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
Destinations to explore
- Downtown Chicago Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- South Side Vacation rentals
- Saugatuck Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Chicago Vacation rentals
- Cabin rentals Chesterton
- House rentals Chesterton
- Rentals with a washer and dryer Chesterton
- Rentals with a fire pit Chesterton
- Family-friendly rentals Chesterton
- Rentals with a patio Chesterton
- Pet-friendly rentals Chesterton
- Rentals with outdoor seating Chesterton
- Kid-friendly rentals Porter County
- Kid-friendly rentals Indiana
- Kid-friendly rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Potato Creek State Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes