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Find Family Hotels in Chesterton, IN

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Check availability on Chesterton Family Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Chesterton family-friendly hotels

Lobby
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1002)
"The hotel was beautiful and new. The issue was that we stayed 3 nights and our room was NEVER cleaned. We had to call the front desk and ask for towels and I emptied the garbage myself and had to ask for them to take it. All the old towels stayed in our bathroom."
United States
Megan
The price is NT$3,531
NT$3,955 total
includes taxes & fees
Jan 11 - 2026/1/12
Hilton Garden Inn Chesterton
2 Double Bed, Lake View | Iron/ironing board, free WiFi, bed sheets
Waterbird Lakeside Inn

Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very Good, (990)
"Balcony was a nice extra. Room was clean and bed was comfortable. I’d stay here again if in the area"
United States
Jorge
Waterbird Lakeside Inn
Lobby
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
8.0 out of 10, Very Good, (1003)
"Nice and close to the beach."
United States
Alison
The price is NT$2,970
NT$3,326 total
includes taxes & fees
Jan 25 - 2026/1/26
Comfort Inn & Suites Porter near Indiana Dunes
Free daily continental breakfast
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
2.5 star property
Chesterton
8.0 out of 10, Very Good, (719)
"Good stay"
Canada
Taesung
The price is NT$2,410
NT$2,700 total
includes taxes & fees
Jan 25 - 2026/1/26
Quality Inn Chesterton near Indiana Dunes National Park I-94
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Chesterton Hotel Reviews

Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

10/10 Excellent
"Great stay"
Ryan 1-night trip
Posted 2 days ago
Baymont by Wyndham New Buffalo

Frequently asked questions

What's Chesterton like for family-friendly vacations?
The relaxing destination of Chesterton is a great choice if you've been considering a vacation with the kids. The beaches, lake views, and coffee shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) from the city center.
What's the best place to stay for a family vacation in Chesterton?
Comfort Inn & Suites Porter near Indiana Dunes is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other good choices for your kid-friendly vacation include Best Western Indian Oak and Hilton Garden Inn Chesterton.
How many hotels that welcome families can I expect to find in Chesterton?
Expedia has 5 family-friendly hotels and other accommodations in Chesterton.
When's the best time to book a family-friendly vacation in Chesterton?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.
What's there to see and do with your family in Chesterton?
While you are visiting Chesterton, you might want to round up the kiddos and make time to see interesting attractions such as Indiana Dunes Visitor Center and Indiana Dunes National Park. Make sure you have lots of time for activities like Chesterton Art Center and Chicago Street Theatre.

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