A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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, (1,004 reviews)
  • cleanliness
    Family adventure resort with indoor pool, sauna, and perfect location for exploring scenic Indiana dunes state parks.
The price is AED 328
AED 367 total
includes taxes & fees
4 Nov - 5 Nov
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, (1,022 reviews)
The price is AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
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, (1,000 reviews)
  • cleanliness
    Family-friendly lakeside inn offers bird watching, clean rooms, and quick access to Indiana Dunes parks.
The price is AED 345
AED 387 total
includes taxes & fees
29 Oct - 30 Oct
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, (872 reviews)
  • cleanliness
    Experience family adventures near Indiana Dunes, where comfortable beds and nature trails create lasting memories.
The price is AED 296
AED 332 total
includes taxes & fees
26 Nov - 27 Nov
Quality Inn Chesterton near Indiana Dunes National Park I-94
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Discover a waterside haven for family adventure with an indoor pool and easy access to Indiana Dunes parks.
The price is AED 373
AED 418 total
includes taxes & fees
28 Nov - 29 Nov
Hilton Garden Inn 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, (116 reviews)
The price is AED 468
AED 524 total
includes taxes & fees
29 Oct - 30 Oct
Furness Mansion
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

7. 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)
  • cleanliness
    Family-friendly fun steps from Indiana Dunes National Park, with an indoor pool, hot tub, and complimentary breakfast for all.
The price is AED 331
AED 370 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Porter near Indiana Dunes
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, (393 reviews)
  • cleanliness
    Family-friendly lodging near Indiana Dunes offers premium TV, free parking, and refrigerators for convenient adventures.
The price is AED 298
AED 333 total
includes taxes & fees
29 Oct - 30 Oct
Fairbridge Inn Express Chesterton
A beach with a parking lot and buildings in the background.

9. Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (139 reviews)
The price is AED 437
AED 572 total
includes taxes & fees
29 Oct - 30 Oct
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

10. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.4 out of 10, Exceptional, (10 reviews)
The price is AED 397
AED 921 total
includes taxes & fees
4 Nov - 5 Nov
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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, (1004)
The price is AED 328
AED 367 total
includes taxes & fees
4 Nov - 5 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, (1004)
The price is AED 328
AED 367 total
includes taxes & fees
4 Nov - 5 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

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"No issue at all will stay here again"
Melissa 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites New Buffalo by IHG

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.