A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chesterton family-friendly hotels

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

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 $125
CA $140 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 traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
A pool area with a round table and chairs, a tiled floor, and large windows.

2. Spring House Inn

Spring House Inn
Chesterton
CA $139
CA $162 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 large windows offering a view of the outside.

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 $132
CA $147 total
includes taxes & fees
Oct 27 - Oct 28
Waterbird Lakeside Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A bar area with a long counter, multiple shelves with bottles, and four bar stools.
A gym with treadmills, elliptical machines, and a dumbbell rack.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

4. 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 $148
CA $166 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Garden Inn Chesterton
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.
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 a flat-screen TV, a mini-fridge, a microwave, a desk with a chair, and a large window with a view.
A hotel room with two beds, a desk, a chair, and a large window.

5. 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 $113
CA $127 total
includes taxes & fees
Nov 26 - Nov 27
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 bedroom with a bed, a desk, a chair, a TV, and a ceiling fan.

6. Furness Mansion

Furness Mansion
Chesterton
CA $171
CA $192 total
includes taxes & fees
Nov 4 - Nov 5
Furness Mansion
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.
A cozy living room with a dark-colored sofa, a round coffee table, and a small side table.
A compact kitchen with white cabinets, a stainless steel refrigerator, a gas stove, and a window with blinds.
A bedroom with a bed, a ceiling fan, two bedside lamps, a black rug, and wooden flooring.

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
CA $151
CA $348 total
includes taxes & fees
Oct 27 - Oct 28
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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 modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.
A dining area with a table set for four, a potted plant, and a kitchen in the background.

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 $167
CA $218 total
includes taxes & fees
Oct 27 - Oct 28
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.
An indoor swimming pool with lounge chairs and a jacuzzi area.
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.

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 $126
CA $141 total
includes taxes & fees
Nov 22 - Nov 23
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.
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.
A bathroom with a toilet, a shower, and a bathtub.

10. 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 $107
CA $119 total
includes taxes & fees
Nov 26 - Nov 27
Fairbridge Inn Express Chesterton
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Choose what matters most at family-friendly hotels in Chesterton

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in Chesterton

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

Best Western Indian Oak

Best Western Indian Oak
Chesterton
CA $125
CA $140 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A brick building with a balcony and green shutters, surrounded by trees.
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.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.

Spring House Inn

Spring House Inn
Chesterton
CA $139
CA $162 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A modern bar area with multiple seating options, including bar stools and round tables with chairs.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A modern reception area with a wooden reception desk, a small seating area, and a snack bar with various packaged goods.

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
CA $148
CA $166 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Garden Inn Chesterton
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.
A reception desk with a blue and white striped design, a sign reading "Quality by Choice Hotels," and a digital screen.
A hallway with a vending machine, a trash bin, and a staircase.
A hotel room with two beds, a desk, a chair, and a large window.

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
Chesterton
CA $113
CA $127 total
includes taxes & fees
Nov 26 - Nov 27
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.
An indoor swimming pool with lounge chairs and a jacuzzi area.
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.

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
CA $126
CA $141 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Porter near Indiana Dunes
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.
A hotel room with a large bed, a desk, a chair, a balcony, and a view of the outdoors.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.
A wooden deck with a railing overlooking a calm lake at sunset.

Best Western Indian Oak

Best Western Indian Oak
Chesterton
CA $125
CA $140 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A brick building with a balcony and green shutters, surrounded by trees.
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.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.

Spring House Inn

Spring House Inn
Chesterton
CA $139
CA $162 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A modern bar area with multiple seating options, including bar stools and round tables with chairs.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A modern reception area with a wooden reception desk, a small seating area, and a snack bar with various packaged goods.

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
CA $148
CA $166 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Garden Inn Chesterton
A reception area with a counter, a vending machine, and a view of the outside through glass doors.
An indoor swimming pool with lounge chairs and a jacuzzi area.
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.

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
CA $126
CA $141 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Porter near Indiana Dunes
A beach with sand dunes and grass.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden play structure with a slide and a small building.

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
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A beach with sand dunes and grass.
A wooden play structure with a slide and a small building.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.
A wooden bridge in a forested area.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
CA $181
CA $234 total
includes taxes & fees
Nov 8 - Nov 9
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.
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Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"Enjoyed my stay with Ameristar"
Cynthinia 1-night trip
Posted less than an hour ago
Ameristar Casino Hotel East Chicago
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The entire staff was kind, friendly and helpful. The hotel was very clean, quiet and welcoming. The continental breakfast had a great variety and the food was delicious. The hotel location was very convenient to many places. I would not hesitate to stay there again! Great visit!!"
Cynthia 2-night trip
Posted 1 hour ago
Holiday Inn Express & Suites New Buffalo by IHG
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Room was clean. Was in town for a wedding and it was close to the venue. Nice spot."
Julissa 2-night trip
Posted 14 hours ago
Best Western Indian Oak
Spring House Inn

Spring House Inn

8/10 Good
"Staff was great and the property had a unique lodge type feel. It was also very close to the Indiana Dunes National and State parks. Only downside is that it desperately needs some maintenance and updating."
Noelle 2-night trip
Posted 16 hours ago
Spring House Inn
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Beautiful room! No microwave and pool was out of service, but still charged a resort fee.. otherwise a great stay."
Olivia 1-night trip
Posted 18 hours ago
Blue Chip Casino Hotel and Spa
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

8/10 Good
"We only spent one night here and slept through breakfast so our experience with anything other than the room itself (very clean and smelling good) was good."
Cathy 1-night trip
Posted 3 weeks ago
Quality Inn Chesterton near Indiana Dunes National Park I-94
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

10/10 Excellent
"Well kept property and the staff were friendly. It was very clean."
Nicole 1-night trip
Posted 3 weeks ago
Comfort Inn & Suites Porter near Indiana Dunes
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 3 weeks ago
Fairfield Inn and Suites By Marriott Merrillville

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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