Kid-friendly vacation rentals in Chesterton

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Popular amenities for Chesterton kid-friendly rentals

Kid-friendly house rentals

Superhost
Home in Chesterton
4.79 out of 5 average rating, 76 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

KieranRating, 5 stars1 month ago
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!
Superhost
Home in Valparaiso
5 out of 5 average rating, 9 reviews

Serene Retreat in Beauty Creek

ErinRating, 5 stars1 week ago
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!
Superhost
Home in Chesterton
4.85 out of 5 average rating, 104 reviews

National Park Nature Lover's Paradise

BarbaraRating, 5 stars1 month ago
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.
Top guest favorite
Home in Chesterton
4.98 out of 5 average rating, 42 reviews

Pool House near the Indiana Dunes

AlaynaRating, 5 stars2 weeks ago
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.
Superhost
Home in Portage
4.88 out of 5 average rating, 26 reviews

Welcome Home

KathyRating, 5 stars4 months ago
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!
Guest favorite
Home in Michigan City
4.96 out of 5 average rating, 397 reviews

Dunefarmhouse Modern Country Escape

EliRating, 5 stars3 weeks ago
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.
Top guest favorite
Home in Portage
4.94 out of 5 average rating, 211 reviews

Newly Renovated with Finished Basement

DestinyRating, 5 stars1 week ago
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
Top guest favorite
Home in Michigan City
5 out of 5 average rating, 38 reviews

New! Charming Retreat in the Heart of MC-King Bed

OliviaRating, 5 stars1 week ago
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

Guest favorite
Apartment in Hammond
4.84 out of 5 average rating, 149 reviews

Plant MOOD FREE Wi-fi, parking, washer & dryer!

AdamRating, 5 stars3 weeks ago
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.
Guest favorite
Apartment in Michigan City
4.9 out of 5 average rating, 102 reviews

Cute 1 bedroom apt near all MC has to offer

SydneyRating, 5 stars3 weeks ago
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!
Top guest favorite
Apartment in Mishawaka
4.96 out of 5 average rating, 485 reviews

Private Entrance Guest Suite on the River

StephenRating, 5 stars3 weeks ago
Great place. I wish I would have gotten there at check-in time, so I could have enjoyed the river more!
Guest favorite
Apartment in Miller
4.83 out of 5 average rating, 229 reviews

Miller Beach Retreat

AmyRating, 5 stars6 days ago
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.
Guest favorite
Apartment in Valparaiso
4.93 out of 5 average rating, 120 reviews

Downtown Apartment on Lincolnway

MorganRating, 5 stars6 days ago
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!
Guest favorite
Apartment in Pilsen Historic District
4.87 out of 5 average rating, 263 reviews

Spectacular Pilsen Studio for 2!

AmitRating, 5 stars1 week ago
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!
Guest favorite
Apartment in Sawyer
4.94 out of 5 average rating, 509 reviews

Cozy Chalet by Lake MI&Dunes with Fire Pit

MadelynRating, 5 stars1 week ago
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!
Top guest favorite
Apartment in South Bend
4.97 out of 5 average rating, 256 reviews

Tiny Retro Studio for One Person

AndrewRating, 5 stars1 week ago
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

Guest favorite
Condo in Wicker Park
4.95 out of 5 average rating, 107 reviews

Modern Izakaya Studio in Wicker Park

KariRating, 5 stars1 week ago
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.
Guest favorite
Condo in Saint Joseph
4.91 out of 5 average rating, 162 reviews

*Luxury condo on water in St Joseph, 2 queen beds*

CassandraRating, 5 stars1 week ago
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!
Top guest favorite
Condo in West Town
4.97 out of 5 average rating, 144 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

AnthonyRating, 5 stars4 days ago
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.
Guest favorite
Condo in Chicago
4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

AngeliqueRating, 5 stars2 weeks ago
Great host and great stay! Beautiful home. Thank you so much!
Guest favorite
Condo in East Rogers Park
4.93 out of 5 average rating, 240 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

JenniferRating, 5 stars6 days ago
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.
Superhost
Condo in Hyde Park
4.83 out of 5 average rating, 173 reviews

Modern Hyde Park Getaway | UChicago

JoãoRating, 5 stars1 month ago
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.
Superhost
Condo in West Town
4.78 out of 5 average rating, 190 reviews

Cabin 301 at 747 Lofts

CiaraRating, 5 stars1 month ago
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 :)
Superhost
Condo in Portage
4.81 out of 5 average rating, 168 reviews

Marina Condo near Lake Michigan

AnnaRating, 5 stars6 months ago
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

Destinations to explore