A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Our top choices for Chesterton family-friendly hotels

A modern building with large windows and balconies, a wooden deck, and a calm lake.

1. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Family adventure resort with indoor pool, sauna, and perfect location for exploring scenic Indiana dunes state parks.
The price is NT$2,934
NT$3,286 total
includes taxes & fees
Nov 22 - Nov 23
Best Western Indian Oak
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.

2. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,004 reviews)
The price is NT$2,984
NT$3,506 total
includes taxes & fees
Nov 30 - Dec 1
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Discover a waterside haven for family adventure with an indoor pool and easy access to Indiana Dunes parks.
The price is NT$4,139
NT$4,636 total
includes taxes & fees
Dec 4 - Dec 5
Hilton Garden Inn Chesterton
A modern bathroom with a large mirror, a bathtub, and a sink.

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Family-friendly lakeside inn offers bird watching, clean rooms, and quick access to Indiana Dunes parks.
The price is NT$3,090
NT$3,461 total
includes taxes & fees
Nov 16 - Nov 17
Waterbird Lakeside Inn
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.

5. 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
7.8 out of 10, Good, (876 reviews)
  • cleanliness
    Experience family adventures near Indiana Dunes, where comfortable beds and nature trails create lasting memories.
The price is NT$2,487
NT$2,786 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn Chesterton near Indiana Dunes National Park I-94
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

6. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
7.8 out of 10, Good, (1,002 reviews)
  • cleanliness
    Family-friendly fun steps from Indiana Dunes National Park, with an indoor pool, hot tub, and complimentary breakfast for all.
The price is NT$2,639
NT$2,956 total
includes taxes & fees
Dec 13 - Dec 14
Comfort Inn & Suites Porter near Indiana Dunes
A large house surrounded by dense forest with a beach and ocean in the background.

7. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (119 reviews)
The price is NT$4,364
NT$4,888 total
includes taxes & fees
Nov 16 - Nov 17
Furness Mansion
A hotel lobby with a red carpet, a bookshelf with books, a potted plant, a table with chairs, a small table with a vase, and a door with a red mat.

8. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (399 reviews)
  • cleanliness
    Family-friendly lodging near Indiana Dunes offers premium TV, free parking, and refrigerators for convenient adventures.
The price is NT$2,722
NT$3,049 total
includes taxes & fees
Nov 29 - Nov 30
Fairbridge Inn Express Chesterton
A swimming pool with a large inflatable frog toy, wooden ceiling, and tiled walls.

9. Country Inn & Suites by Radisson, Portage, IN

Country Inn & Suites by Radisson, Portage, IN
3.0 star property
Portage
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Family-friendly hotel brings smiles to children's faces with an indoor pool, playground, and game room near Indiana Dunes National Park.
The price is NT$4,635
NT$5,192 total
includes taxes & fees
Dec 10 - Dec 11
Country Inn & Suites by Radisson, Portage, IN
A casino with multiple slot machines, a large spinning wheel, and neon-lit signs.

10. Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa
3.5 star property
Michigan City
8.4 out of 10, Very good, (2,432 reviews)
  • cleanliness
    Family-friendly getaway with indoor pool and casino offers endless entertainment for all ages with nearby beach access.
The price is NT$2,788
NT$3,674 total
includes taxes & fees
Nov 29 - Nov 30
Blue Chip Casino Hotel and Spa
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.
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Choose what matters most at family-friendly hotels in Chesterton

Breakfast included
Pool

Family-friendly hotels with free breakfast in Chesterton

A modern building with large windows and balconies, a wooden deck, and a calm lake.
Best Western Indian Oak

Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1003)
The price is NT$2,934
NT$3,286 total
includes taxes & fees
Nov 22 - Nov 23
Best Western Indian Oak
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

Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Rooms were clean, staff was helpful and pleasant. No hot tub or breakfast available. Balcony on the Lake Michigan was awesome. Overall a nice experience. We would stay there again. No elevator so I requested the first floor. No fun taking luggage up stairs."
ANGEL 1-night trip
Posted 15 hours ago
Waterbird Lakeside Inn

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?
Best Western Indian Oak 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 Hilton Garden Inn Chesterton and Quality Inn Chesterton near Indiana Dunes National Park I-94.
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 Port of Indiana-Burns Harbor.

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