A wooden staircase ascending a sandy hill with sparse vegetation.

Find Family Hotels in Chesterton, IN

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Family Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Chesterton family-friendly hotels

A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.

1. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,001 reviews)
"It was a nice change from the normal big hotels. Small and quaint. Would definitely stay again!!"
United States
Nathaniel
The price is AED 364
AED 426 total
includes taxes & fees
2 Nov - 3 Nov
Spring House Inn
A modern building with large windows and balconies, a wooden deck, and a calm lake.

2. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,002 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
The price is AED 328
AED 367 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Indian Oak
A modern bathroom with a large mirror, a bathtub, and a sink.

3. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,002 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
The price is AED 345
AED 387 total
includes taxes & fees
2 Nov - 3 Nov
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.

4. 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, (873 reviews)
"Clean room, friendly staff, easy parking, lots of restaurants and coffee shops in the area."
United States
Nikola
The price is AED 278
AED 311 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn Chesterton near Indiana Dunes National Park I-94
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.

5. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (396 reviews)
"Friendly staff great locatikn"
United States
Kayla
The price is AED 283
AED 317 total
includes taxes & fees
1 Dec - 2 Dec
Fairbridge Inn Express Chesterton
A large house surrounded by dense forest with a beach and ocean in the background.

6. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (117 reviews)
"Staff was extremely helpful and responded promptly. The room was very clean, and inviting. Great location for the beaches or short trips to Michigan."
United States
Bryan
The price is AED 463
AED 519 total
includes taxes & fees
2 Dec - 3 Dec
Furness Mansion
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

7. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,002 reviews)
"Excellent hotel, friendly staff"
United States
Cheryl
The price is AED 368
AED 412 total
includes taxes & fees
28 Nov - 29 Nov
Hilton Garden Inn Chesterton
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

8. 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, (1,000 reviews)
"Good one night stay. Nice to have breakfast there before we headed out."
United States
Julie Van
The price is AED 323
AED 362 total
includes taxes & fees
1 Dec - 2 Dec
Comfort Inn & Suites Porter near Indiana Dunes
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

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, (1002)
The price is AED 328
AED 367 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Indian Oak
View all properties

Family-friendly hotels with pools 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, (1002)
The price is AED 328
AED 367 total
includes taxes & fees
16 Nov - 17 Nov
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

Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"Love the view from the balcony overlooking the small lake. Very basic motel, but clean and perfect for the night."
Katherine 1-night trip
Posted 1 day ago
Best Western Indian Oak

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.