A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
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 wooden deck with a railing overlooking a calm lake at sunset.
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.

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.
NT$2,708
NT$3,033 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
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 bathroom with a toilet, sink, mirror, and shower curtain.

2. 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.
NT$2,750
NT$3,080 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn Chesterton near Indiana Dunes National Park I-94
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 bar area with a long counter, multiple shelves with bottles, and four bar stools.
A gym with treadmills, elliptical machines, and a dumbbell rack.

3. 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.
NT$4,232
NT$4,740 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A modern bathroom with a large mirror, a bathtub, and a sink.
A spacious lobby with a staircase, a reception desk, and a chandelier.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.
A spacious lobby with a staircase, a reception desk, and large windows offering a view of the outside.

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Family-friendly lakeside inn offers bird watching, clean rooms, and quick access to Indiana Dunes parks.
NT$2,995
NT$3,354 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
A reception area with a counter, a vending machine, and a view of the outside through glass doors.
A hotel room with a large bed, a bedside table with a lamp, a bathroom with a bathtub, and a window with curtains.
A hotel with a covered entrance, multiple windows, and a parking lot.
A modern kitchen with a coffee station, a bread display, and a refrigerated display.

5. 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.
NT$2,980
NT$3,337 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Porter near Indiana Dunes
A large house surrounded by dense forest with a beach and ocean in the background.
A bedroom with a bed, a desk, a chair, a TV, and a ceiling fan.
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.

6. Furness Mansion

Furness Mansion
Chesterton
NT$4,230
NT$4,737 total
includes taxes & fees
Oct 5 - Oct 6
Furness Mansion
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 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.
NT$2,581
NT$2,890 total
includes taxes & fees
Oct 20 - Oct 21
Fairbridge Inn Express Chesterton
A swimming pool with a large inflatable frog toy, wooden ceiling, and tiled walls.
A modern living room with a fireplace, two sofas, a coffee table, and a wooden wall.
A hotel room with a bed, a sofa, a desk, and a TV.
A modern kitchen with a central island, blue cabinets, and a variety of kitchen appliances.

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

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.
NT$4,441
NT$4,974 total
includes taxes & fees
Oct 13 - Oct 14
Country Inn & Suites by Radisson, Portage, IN
A swimming pool with three orange chairs and a blue wall with windows.
A modern Hampton Inn & Suites building with a well-lit entrance and a large tree in front.
A modern reception area with a reception desk, a welcome sign, and a large glass door leading outside.
A hotel room with a wooden desk, a flat-screen TV, a chair, a microwave, and a large window.

9. Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso
Valparaiso
NT$3,893
NT$4,360 total
includes taxes & fees
Oct 11 - Oct 12
Hampton Inn & Suites Valparaiso
A modern hotel lobby with a curved seating area, a reception desk, and a television mounted on the wall.
A hotel room with two beds, a desk with a TV, a window with curtains, and a wall-mounted headboard.
A breakfast bar with a coffee machine, a toaster, and a display case with pastries.
A modern hotel room with a glass-top coffee table, orange seating, a flat-screen TV, and a framed picture on the wall.

10. Best Western University Inn At Valparaiso

Best Western University Inn At Valparaiso
Valparaiso
  • Experience family-friendly magic at this Valparaiso hotel with free activities, cribs, and premium TV channels for all ages.
NT$3,473
NT$3,890 total
includes taxes & fees
Oct 5 - Oct 6
Best Western University Inn At Valparaiso
View all properties

Choose what matters most at family-friendly hotels in Chesterton

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chesterton Hotel Reviews

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The pool stayed open until 12am for adults ONLY!"
Natalya 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites New Buffalo by IHG
Spring House Inn

Spring House Inn

8/10 Good
"I love the location of this place- it's very conveniently located but surrounded by trees, water and residential areas so feels more quiet & secluded, and just a little different, in a good way, from the big chains. Sauna and heated indoor pool were nice amenities though the pool area did run out of clean towels in the evening. Breakfast was basic but decent. Also liked there were common areas for people to gather. This property is older but well maintained and clean. We missed a couple things, like no in-room coffee maker, laundry bag for wet clothes, and there was only one wheeled chair in the room so not enough seating besides beds. But overall, the stay was great and would absolutely stay again. Also a bonus to have a restaurant right next door (Uno Pizzeria) that has live music some nights (piano)!"
Michelle 2-night trip
Posted 6 hours ago
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"Everything was solid for the price. Comfortable and decent, with a nice view close to the Dunes."
Joseph 2-night trip
Posted 1 day ago
Best Western Indian Oak
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

8/10 Good
"clean room, cute little pool area, a/c worked good."
Chad 1-night trip
Posted 3 days ago
Quality Inn Near Interstate I94
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

10/10 Excellent
"Very nice for the price.."
James 1-night trip
Posted 5 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 5 days ago
Waterbird Lakeside Inn
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

8/10 Good
"Breakfast was great! Hot tub was wonderful! Pool looked nice! Convenient location, a little noisy from cars and trains."
Kathleen 1-night trip
Posted 6 days ago
Comfort Inn & Suites Porter near Indiana Dunes

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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