A wooden staircase ascending a sandy hill with sparse vegetation.

Find Family Hotels in Chesterton, IN from CA $129

  • 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

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chesterton family-friendly hotels

A modern building with large windows and balconies, a wooden deck, and a calm lake.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.
A wooden deck with a railing overlooking a calm lake at sunset.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.

1. Best Western Indian Oak

Best Western Indian Oak
Chesterton
  • Family adventure resort with indoor pool, sauna, and perfect location for exploring scenic Indiana dunes state parks.
CA $121
CA $136 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a television.
A pool area with a round table and chairs, a tiled floor, and large windows.
A spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.

2. Spring House Inn

Spring House Inn
Chesterton
CA $106
CA $126 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A modern bathroom with a large mirror, a bathtub, and a sink.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.
A wooden deck with two white plastic chairs facing a calm lake and forested hills.
A spacious lobby with a staircase, a reception desk, and a chandelier.

3. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Family-friendly lakeside inn offers bird watching, clean rooms, and quick access to Indiana Dunes parks.
CA $134
CA $150 total
includes taxes & fees
Oct 26 - Oct 27
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.
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.
A reception desk with a blue and white striped design, a sign reading "Quality by Choice Hotels," and a digital screen.
A hotel room with two beds, a desk, a chair, and a large window.

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

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.
CA $123
CA $138 total
includes taxes & fees
Nov 5 - Nov 6
Quality Inn Chesterton near Indiana Dunes National Park I-94
A large house surrounded by dense forest with a beach and ocean in the background.
A living room with two wicker chairs, a small table, and a grey sofa.
A corner room with two wicker chairs, a small table, and a bay window with a view of trees.
A dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.

5. Furness Mansion

Furness Mansion
Chesterton
CA $172
CA $193 total
includes taxes & fees
Oct 7 - Oct 8
Furness Mansion
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A gym with treadmills, elliptical machines, and a dumbbell rack.
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.

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
  • Discover a waterside haven for family adventure with an indoor pool and easy access to Indiana Dunes parks.
CA $188
CA $211 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
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 hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

7. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
Chesterton
  • Family-friendly lodging near Indiana Dunes offers premium TV, free parking, and refrigerators for convenient adventures.
CA $115
CA $129 total
includes taxes & fees
Oct 7 - Oct 8
Fairbridge Inn Express Chesterton
A beach with a parking lot and buildings in the background.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.
A dining area with a table set for four, a potted plant, and a kitchen in the background.
A bathroom with a toilet, sink, and shower.

8. 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
CA $170
CA $222 total
includes taxes & fees
Oct 7 - Oct 8
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A reception area with a counter, a vending machine, and a view of the outside through glass doors.
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.
An indoor swimming pool with lounge chairs and a jacuzzi area.

9. Comfort Inn & Suites Porter near Indiana Dunes

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.
CA $122
CA $137 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Porter near Indiana Dunes
A wooden play structure with a slide and a small building.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.
A two-story building with a white exterior and a covered porch.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.

10. The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
CA $284
CA $358 total
includes taxes & fees
Oct 7 - Oct 8
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
View all properties

Choose what matters most at family-friendly hotels in Chesterton

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with pools in Chesterton

A modern building with large windows and balconies, a wooden deck, and a calm lake.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.
A wooden deck with a railing overlooking a calm lake at sunset.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.

Best Western Indian Oak

Best Western Indian Oak
Chesterton
CA $121
CA $136 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A beach with sand dunes and grass.
A two-story building with a white exterior and a covered porch.
A wooden play structure with a slide and a small building.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
CA $284
CA $358 total
includes taxes & fees
Oct 7 - Oct 8
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A reception area with a counter, a vending machine, and a view of the outside through glass doors.
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.
An indoor swimming pool with lounge chairs and a jacuzzi area.

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
CA $122
CA $137 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Porter near Indiana Dunes
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A modern bar area with multiple seating options, including bar stools and round tables with chairs.

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
CA $188
CA $211 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A beach with sand dunes and grass.
A wooden bridge in a forested area.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
CA $184
CA $238 total
includes taxes & fees
Oct 7 - Oct 8
The "Pool Barn Camper" w/Hot Tub 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

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Everything was great! Staff is very nice!"
David 1-night trip
Posted 2 hours ago
Blue Chip Casino Hotel and Spa
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"The room was spacious, extremely clean and had a beautiful bathroom. Great parking and professional front desk staff. Would give 5 stars except for the fact it smelled like weed in several places throughout the hotel, unfortunately."
Joane 1-night trip
Posted 8 hours ago
Ameristar Casino Hotel East Chicago
Fairfield Inn and Suites By Marriott Merrillville

Fairfield Inn and Suites By Marriott Merrillville

10/10 Excellent
"Great experience i had in a long time"
Steve 2-night trip
Posted 14 hours ago
Fairfield Inn and Suites By Marriott Merrillville
Spring House Inn

Spring House Inn

10/10 Excellent
"Excellent experience"
Sukhwinder 2-night trip
Posted 23 hours ago
Spring House Inn
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

10/10 Excellent
"Very nice for the price.."
James 1-night trip
Posted 6 days ago
Fairbridge Inn Express Chesterton
Waterbird Lakeside Inn

Waterbird Lakeside Inn

8/10 Good
"The room was clean and very comfortable!! And the view was the best!"
Barry 2-night trip
Posted 7 days 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.

Explore a world of travel with Expedia