
Kid-friendly vacation rentals in Chesterton
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Top-rated kid-friendly rentals in Chesterton
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
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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
Such a beautiful townhome. It was a perfect place to get ready for my wedding. Beautiful decor and lots of natural light. It was a lovely space. 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.

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!

Dunefarmhouse Modern Country Escape
This is such a beautiful home! Got the chance to unplug and feel right at home within the trees. Lots to do in the area too, went to the zoo, winery, and a brewery. Laurel was great and had a bunch of notes around the home that were super informative and helpful. I would absolutely recommend this place to anyone who’s looking to slow things down and connect with nature.

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

New! Charming Retreat in the Heart of MC-King Bed
Eileen was a great host! The space was beautiful and plenty for my husband and our two kids. She was extremely responsive and went above and beyond to make sure our stay was great. Highly recommend if you’re looking to stay in Michigan City!
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!

Spectacular Pilsen Studio for 2!
Hena was super attentive and reached out to check in a few times during our trip. The apartment was clean and comfortable and a great place from which to explore Pilsen or hop on bikes and head up into the busier parts of the city. Thanks for a great trip!

Cozy Chalet by Lake MI&Dunes with Fire Pit
We had an awesome stay at Hannah’s. She went above and beyond to make sure we were comfortable and we loved all the recommendations she shared with us. We would stay again!

Tiny Retro Studio for One Person
Really great place to stay. Everything that you need to make simple meal if you don’t want to eat out all the time. Restaurants close by that you can walk to. Place is clean.
Kid-friendly condo rentals

Modern Izakaya Studio in Wicker Park
My daughter and I stayed at Izakaya Studio on a recent visit to Chicago. The studio is great and Brett made it so easy to locate everything we needed to make our stay enjoyable. The next time we stay I hope to spend more time exploring the neighborhood because there were so many restaurants and shops to choose from (lots of open-air patios and decks which would be so nice during the summer season). The walk to the blue line El stop felt safe and quick. We loved the studio's layout. The kitchen and bedroom areas were separate and Brett has two big, comfy chairs for relaxing, and ample island space for eating or using as a work space. My daughter had some virtual work meetings and the Wi-Fi was reliable. The kitchen was well stocked with everything you'd need for meal prep. We ate out each day, but our delicious breakfast take-out came from a place right up the street called Yolk. I highly recommend the Izakaya Studio for a relaxing and fun visit to Chicago.

*Luxury condo on water in St Joseph, 2 queen beds*
Kirstin was great! The place was gorgeous and the perfect location! I also felt extremely safe in the location we were at. The jacuzzi tub was the perfect way to relax after a long day of walking!! I’d definitely stay again!

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

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

Cozy 1bdr Rogers Park, Loyola, Northwestern.
This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.

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.

Cabin 301 at 747 Lofts
Affordable, quick & easy booking / check-in & check-out…it’s great spot for a quick trip to chicago for a night or two! We used the parking lot area across the alleyway, rented one of the spot hero spaces which was not the most convenient parking situation but it’s the city sooo kinda usual! The ONLY thing i wish that had been mentioned was that it was right next door to a fire dept. one pair of ear plugs were provided but just ya wish i had researched the location just a lil bit more… thanks again for welcoming us to stay :)

Marina Condo near Lake Michigan
Met our needs very well. There was a little restaurant on the premesis.
Quick stats about vacation rentals that are kid-friendly in Chesterton
Total rentals
20 properties
Nightly prices starting at
G$14,640 GYD 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
- 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