The Best Family Hotels in Chesterton, IN from ₩68,238 in 2026

A wooden staircase ascending a sandy hill with sparse vegetation.

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Our top choices for Chesterton family-friendly hotels

A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.

A hotel room with two beds, a desk, a chair, and a large window.

A bathroom with a toilet, sink, mirror, and shower curtain.

A hotel room with a flat-screen TV, a mini-fridge, a microwave, a desk with a chair, and a large window with a view.

1. Quality Inn Chesterton near Indiana Dunes National Park I-94

Chesterton

Experience family adventures near Indiana Dunes, where comfortable beds and nature trails create lasting memories.

₩123,228

₩138,015 total

includes taxes & fees

Oct 11 - Oct 12

A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

A hotel room with a dining area, a sofa, a TV, and a microwave.

A bar area with a long counter, multiple shelves with bottles, and four bar stools.

A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

2. Hilton Garden Inn Chesterton

Chesterton

Discover a waterside haven for family adventure with an indoor pool and easy access to Indiana Dunes parks.

₩198,131

₩221,906 total

includes taxes & fees

Sep 20 - Sep 21

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.

A bathroom with a toilet, a shower, and a bathtub.

A reception area with a red carpet, patterned chairs, a clock, and a counter with informational signs.

A laundry area with washers and dryers, a trash bin, a red rug, and a dining area with chairs and a table.

3. Fairbridge Inn Express Chesterton

Chesterton

Family-friendly lodging near Indiana Dunes offers premium TV, free parking, and refrigerators for convenient adventures.

₩109,338

₩122,459 total

includes taxes & fees

Oct 1 - Oct 2

A reception area with a counter, a vending machine, and a view of the outside through glass doors.

A modern kitchen with a coffee station, a bread display, and a refrigerated display.

A hotel with a covered entrance, multiple windows, and a parking lot.

A hotel room with a large bed, a bedside table with a lamp, a bathroom with a bathtub, and a window with curtains.

4. Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

Family-friendly fun steps from Indiana Dunes National Park, with an indoor pool, hot tub, and complimentary breakfast for all.

₩155,989

₩174,709 total

includes taxes & fees

Oct 8 - Oct 9

A two-story house with a stone chimney, a brick exterior, and a front porch with a bench.

A dining area with a wooden table set for six, surrounded by white chairs. There is a sofa and a piano in the background.

A modern living room with a fireplace, a dining area, and a bookshelf.

A bedroom with a bed, a ceiling fan, a window with curtains, a nightstand, and a painting on the wall.

5. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Chesterton

₩397,980

₩812,924 total

includes taxes & fees

Sep 27 - Sep 28

A swimming pool with a large inflatable frog toy, wooden ceiling, and tiled walls.

A multi-story hotel with a covered entrance and stone pillars.

A modern kitchen with a central island, blue cabinets, and a variety of kitchen appliances.

A modern living room with a fireplace, two sofas, a coffee table, and a wooden wall.

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

Portage

Family-friendly hotel brings smiles to children's faces with an indoor pool, playground, and game room near Indiana Dunes National Park.

₩177,843

₩199,184 total

includes taxes & fees

Sep 27 - Sep 28

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Choose what matters most at family-friendly hotels in Chesterton

Breakfast included

Pool

All-inclusive

4 stars

5 stars

Top Chesterton Hotel Reviews

Fairbridge Inn Express Chesterton

8/10 Good

"Decent rooms with all the basic amenities. Biggest advantage is its proximity to all the major tourist destinations and convenience stores nearby."

Ameristar Casino Hotel East Chicago

10/10 Excellent

"Wonderful hotel"

Blue Chip Casino Hotel and Spa

10/10 Excellent

"It was my first time only thing that it wasn’t a microwave in the room everything was Nice"

Microtel Inn & Suites by Wyndham Michigan City

8/10 Good

"Good enough for stay. Breakfast is sufficient. The pool unfortunately is not available during our stay."

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent

"I did not like to see so many cannabis stores within walking distance of our hotel.."

Comfort Inn Hammond I-94

10/10 Excellent

"Nice"

Baymont by Wyndham New Buffalo

10/10 Excellent

"Hair dryer was broke and AC water was leaking from the room upper room. The staff changed my room. It was ok."

Hilton Garden Inn Chesterton

10/10 Excellent

"Perfect"

Spring House Inn

10/10 Excellent

"This place was awesome!! We’ll be staying at this place when we go up there from now on."

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 Comfort Inn & Suites Porter near Indiana Dunes 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 Chicago Street Theatre.

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Book Family Hotels in Chesterton on Expedia.com

Find Family Hotels in Chesterton, IN

Change your mind

Treat yourself

Be picky

Check availability on Chesterton Family Hotels

Our top choices for Chesterton family-friendly hotels

1. Quality Inn Chesterton near Indiana Dunes National Park I-94

2. Hilton Garden Inn Chesterton

3. Fairbridge Inn Express Chesterton

4. Comfort Inn & Suites Porter near Indiana Dunes

5. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

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

Choose what matters most at family-friendly hotels in Chesterton

Top Chesterton Hotel Reviews

Fairbridge Inn Express Chesterton

Ameristar Casino Hotel East Chicago

Blue Chip Casino Hotel and Spa

Microtel Inn & Suites by Wyndham Michigan City

Holiday Inn Express & Suites New Buffalo by IHG

Comfort Inn Hammond I-94

Baymont by Wyndham New Buffalo

Hilton Garden Inn Chesterton

Spring House Inn

Frequently asked questions

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