A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chesterton family-friendly hotels

A modern building with large windows and balconies, a wooden deck, and a calm lake.
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.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.

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.
AED 312
AED 350 total
includes taxes & fees
1 Nov - 2 Nov
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 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
AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House 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 bathroom with a toilet, sink, mirror, and shower curtain.

3. 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.
AED 301
AED 337 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn Chesterton near Indiana Dunes National Park I-94
A modern bathroom with a large mirror, a bathtub, and a sink.
A spacious lobby with a staircase, a reception desk, and large windows offering a view of the outside.
A wooden deck with two white plastic chairs facing a calm lake and forested hills.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Family-friendly lakeside inn offers bird watching, clean rooms, and quick access to Indiana Dunes parks.
AED 345
AED 387 total
includes taxes & fees
26 Oct - 27 Oct
Waterbird Lakeside Inn
A large house surrounded by dense forest with a beach and ocean in the background.
A dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.
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.

5. Furness Mansion

Furness Mansion
Chesterton
AED 414
AED 464 total
includes taxes & fees
12 Nov - 13 Nov
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 bathroom with a toilet, a shower, and a bathtub.
A laundry area with washers and dryers, a trash bin, a red rug, and a dining area with chairs and a table.
A reception area with a red carpet, patterned chairs, a clock, and a counter with informational signs.

6. 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.
AED 274
AED 307 total
includes taxes & fees
16 Nov - 17 Nov
Fairbridge Inn Express Chesterton
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.

7. 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.
AED 404
AED 452 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chesterton
A wooden play structure with a slide and a small building.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.
A beach with sand dunes and grass.

8. 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
AED 731
AED 926 total
includes taxes & fees
18 Oct - 19 Oct
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 modern kitchen with a coffee station, a bread display, and a refrigerated display.
An indoor swimming pool with lounge chairs and a jacuzzi area.
A hotel with a covered entrance, multiple windows, and a parking lot.

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.
AED 334
AED 374 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Porter near Indiana Dunes
A beach with a parking lot and buildings in the background.
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.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.

10. 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
AED 437
AED 572 total
includes taxes & fees
22 Oct - 23 Oct
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
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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 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 spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.

Spring House Inn

Spring House Inn
Chesterton
AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
A modern building with large windows and balconies, a wooden deck, and a calm lake.
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.
A hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.

Best Western Indian Oak

Best Western Indian Oak
Chesterton
AED 312
AED 350 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Indian Oak
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
AED 404
AED 452 total
includes taxes & fees
9 Nov - 10 Nov
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 hallway with a vending machine, a trash bin, and a staircase.
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.

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
Chesterton
AED 301
AED 337 total
includes taxes & fees
16 Nov - 17 Nov
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.
A modern kitchen with a coffee station, a bread display, and a refrigerated display.
An indoor swimming pool with lounge chairs and a jacuzzi area.
A hotel with a covered entrance, multiple windows, and a parking lot.

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
AED 334
AED 374 total
includes taxes & fees
8 Nov - 9 Nov
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.
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Top Chesterton Hotel Reviews

Spring House Inn

Spring House Inn

8/10 Good
"Nice setting. The room was clean. The staff was helpful and pleasant. The breakfast was good with hot and cold options. The downsides which are not the fault of the Spring House Inn, was that the most direct route to the hotel was closed due to a bridge being rebuilt and there were train noises throughout the night which made it hard to sleep."
Victoria 2-night trip
Posted 14 hours ago
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Good location, easy access and parking. Staff friendly and helpful. Room decent sized and breakfast decent. Only stayed one night as was passing though. Would stay again."
Steve 1-night trip
Posted 14 hours ago
Best Western Indian Oak
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The hotel is clean, comfortable, great location near I94 and good restaurants, serves a good breakfast."
Susan 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites New Buffalo by IHG
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

10/10 Excellent
"Debbie was the most beautiful and warm hearted person we have met in town. From the very moment we were looking to park our trailer she step out and guided us through. She gave us a warm welcome and guided us through everything. She would make sure we are situated in. Will be back soon!!"
Jazmine 2-night trip
Posted 6 days ago
Fairbridge Inn Express Chesterton
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 8 days 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 8 days ago
Comfort Inn & Suites Porter near Indiana Dunes
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Hotel was minutes from Indiana state and National Dunes parks. There were two restaurants within walking distance and a gas station across the street. But it was the people at the hotel that made it. And the bartender makes a great margarita. Definitely stay here!"
Michele 1-night trip
Posted 9 days ago
Hilton Garden Inn Chesterton

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.