A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.
A bedroom with a bed, a desk, a chair, a television, and a ceiling fan.
A bedroom with a bed, a ceiling fan, a fireplace, and a television.
A bedroom with a bed, a ceiling fan, a window, a desk, and a chair.

1. Full House booking of a history building close to the Dunes

Full House booking of a history building close to the Dunes
Chesterton
￥280,540
￥358,991 total
includes taxes & fees
Oct 6 - Oct 7
Full House booking of a history building close to the Dunes
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.
A compact kitchen with grey cabinets, a wooden countertop, and a coffee maker.
A two-story house with a porch, a garage, and a wooded backdrop.
A modern kitchen with a central island, stainless steel appliances, and a clock on the wall.

2. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,031
￥61,536 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
A beach with sand dunes and grass.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A two-story building with a white exterior and a covered porch.
A wooden play structure with a slide and a small building.

3. 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
￥31,317
￥39,658 total
includes taxes & fees
Oct 7 - Oct 8
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
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 modern reception area with a wooden reception desk, a small seating area, and a snack bar with various packaged goods.
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
￥20,655
￥23,134 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A beach with a sunset, waves, and sparse vegetation.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.
An outdoor patio with a gray sofa set, a barbecue grill, and a hot tub.
A bedroom with a bed, pillows, a ceiling fan, and a wardrobe.

5. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
￥22,670
￥48,489 total
includes taxes & fees
Oct 8 - Oct 9
Tower Haus w/Private Hot Tub
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 hotel room with a bed, a bathroom with a bathtub, a desk, and a chair.
A spacious lobby with multiple seating areas, a staircase, and a large window providing natural light.

6. Best Western Indian Oak

Best Western Indian Oak
Chesterton
  • Serene lakeside luxury with spectacular views, indoor pool, and sauna near Indiana Dunes National Park.
￥13,380
￥14,986 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.
A living room with a flat-screen TV mounted on the wall, a sofa, a coffee table with books and a bottle, and a window with a view of the outside.
A bedroom with a bed, two windows, a nightstand, and a patterned rug.

7. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
￥20,743
￥63,786 total
includes taxes & fees
Oct 6 - Oct 7
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | 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 dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.
A corner room with two wicker chairs, a small table, and a bay window with a view of trees.

8. Furness Mansion

Furness Mansion
Chesterton
￥19,227
￥21,534 total
includes taxes & fees
Oct 8 - Oct 9
Furness Mansion
A beach with sand dunes and grass.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden bridge in a forested area.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,308
￥26,271 total
includes taxes & fees
Oct 4 - Oct 5
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.
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.
A compact kitchen with a built-in oven, a refrigerator, and a television mounted on the oven.

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
￥19,679
￥42,670 total
includes taxes & fees
Oct 26 - Oct 27
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
View all properties

Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
"Room was excellent and staffeas helpful"
Gerardo 2-night trip
Posted 17 hours ago
Ameristar Casino Hotel East Chicago
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Very nice hotel but some restaurants not open, smocking smell too strong"
Ken 1-night trip
Posted 1 day ago
Blue Chip Casino Hotel and Spa
Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"Very clean room. Friendly, helpful staff, even at 9pm. Balcony was amazing to watch the sunrise. Had a little trouble with the shower head but maintenance will get to it before we return for our next visit. We absolutely will be back."
Bryana 1-night trip
Posted 1 day ago
Best Western Indian Oak
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 2 days ago
Waterbird Lakeside Inn

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Chesterton?
Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesterton offers. Known for its restaurants, Chesterton also has some interesting things to see and do including Lake Michigan, so you may want to take in the local sights during your visit.
When can I expect good weather in Chesterton?
Planning for the weather is an important factor for making your trip to Chesterton a success, especially when you're splurging. 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 in Chesterton?
Enjoy Chesterton and visit Lake Michigan, Lustron House, and Indiana Dunes Visitor Center. If you have extra time while you're in the area, you might want to see Bailly Homestead - American Indians and Fur Traders and Indiana Dunes National Park.

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