A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Family Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 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.
AED 328
AED 367 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 spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.
A pool area with a round table and chairs, a tiled floor, and large windows.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.

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 bathroom with a large mirror, a bathtub, and a sink.
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.
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.
AED 345
AED 387 total
includes taxes & fees
25 Oct - 26 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.
A bathroom with a toilet, sink, mirror, and shower curtain.
A hotel room with two beds, a desk, a chair, and a large window.
A reception desk with a blue and white striped design, a sign reading "Quality by Choice Hotels," and a digital screen.

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.
AED 311
AED 348 total
includes taxes & fees
8 Nov - 9 Nov
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 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.

5. Furness Mansion

Furness Mansion
Chesterton
AED 453
AED 508 total
includes taxes & fees
26 Oct - 27 Oct
Furness Mansion
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A gym with treadmills, elliptical machines, and a dumbbell rack.
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.
AED 398
AED 445 total
includes taxes & fees
16 Nov - 17 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 beach with sand dunes and grass.
A two-story building with a white exterior and a covered porch.

7. 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
25 Oct - 26 Oct
The "Pool Barn" w/Pool, Hot Tub, Billiards & more 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 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.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

8. 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 277
AED 310 total
includes taxes & fees
22 Nov - 23 Nov
Fairbridge Inn Express Chesterton
A beach with a parking lot and buildings in the background.
A bathroom with a toilet, sink, and shower.
A dining area with a table set for four, a potted plant, and a kitchen in the background.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

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
AED 437
AED 572 total
includes taxes & fees
26 Oct - 27 Oct
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.

10. 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 330
AED 370 total
includes taxes & fees
19 Nov - 20 Nov
Comfort Inn & Suites Porter 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 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 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
AED 328
AED 367 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Indian Oak
A brick building with a balcony and green shutters, surrounded by trees.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
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.

Spring House Inn

Spring House Inn
Chesterton
AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
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
AED 398
AED 445 total
includes taxes & fees
16 Nov - 17 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 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.
A reception desk with a blue and white striped design, a sign reading "Quality by Choice Hotels," and a digital screen.

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
Chesterton
AED 311
AED 348 total
includes taxes & fees
8 Nov - 9 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.
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
AED 330
AED 370 total
includes taxes & fees
19 Nov - 20 Nov
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 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
AED 328
AED 367 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Indian Oak
A brick building with a balcony and green shutters, surrounded by trees.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
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.

Spring House Inn

Spring House Inn
Chesterton
AED 364
AED 426 total
includes taxes & fees
1 Nov - 2 Nov
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
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
AED 398
AED 445 total
includes taxes & fees
16 Nov - 17 Nov
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
AED 330
AED 370 total
includes taxes & fees
19 Nov - 20 Nov
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
AED 731
AED 926 total
includes taxes & fees
25 Oct - 26 Oct
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A beach with sand dunes and grass.
A wooden bridge in a forested area.
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.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
AED 474
AED 613 total
includes taxes & fees
1 Nov - 2 Nov
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

Spring House Inn

Spring House Inn

8/10 Good
"Unique older hotel in the area of Indiana Dunes NP. The facility has been around for a while...age shows but the bones are good. Modernization would ruin the ambiance! Rooms are huge, clean, and functional. However, they are dimly lit and dated. The hotel is filled with antiques and live plants...a rarity...but they burn candles to mask musty odors...I assume...as there was an odd odor the first day we arrived. Breakfast was the usual hotel fix it your self breakfast. Nothing special but good for included. Parking area could use some sprucing up. I would stay again if in the area."
Sandra 2-night trip
Posted 17 hours ago
Spring House Inn
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Great stay. Reasonable price."
Sandra 2-night trip
Posted 3 days ago
Waterbird Lakeside Inn
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Very nice room. Lake view was nice. Breakfast was good."
Ruth 1-night trip
Posted 4 days ago
Best Western Indian Oak
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 13 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 2 weeks 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.