A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
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 large bed, two bedside tables, a ceiling fan, and a chair.
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
￥281,289
￥359,949 total
includes taxes & fees
Oct 6 - Oct 7
Full House booking of a history building close to the Dunes
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.

2. 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
￥31,412
￥39,778 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 spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a dining area, a sofa, a TV, and a microwave.
A modern bar area with multiple seating options, including bar stools and round tables with chairs.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥21,357
￥23,920 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Chesterton
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 bedroom with a bed, a nightstand, a ceiling fan, a window with curtains, and a view of greenery outside.
A two-story house with a porch, a garage, and a wooded backdrop.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,098
￥61,700 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
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 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.

5. Furness Mansion

Furness Mansion
Chesterton
￥19,069
￥21,357 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.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,363
￥26,342 total
includes taxes & fees
Oct 6 - Oct 7
The "Pool Barn Camper" w/Hot Tub 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 bedroom with a bed, bedside tables, a nightstand, a window, and a bathroom with a bathtub.
A dining area with a table set for four, a potted plant, and a kitchen in the background.

7. 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
￥18,784
￥24,574 total
includes taxes & fees
Oct 6 - Oct 7
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
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 spacious lobby with a staircase, a reception desk, and a chandelier.
A wooden deck with two white plastic chairs facing a calm lake and forested hills.

8. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Lakeside luxury thrives at this Chesterton retreat where private balconies frame serene water views and wildlife encounters.
￥14,836
￥16,617 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
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 cozy living room with a dark-colored sofa, a round coffee table, and a small side table.
A compact kitchen with a built-in oven, a refrigerator, and a television mounted on the oven.

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
￥15,785
￥37,657 total
includes taxes & fees
Nov 4 - Nov 5
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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 large bed, a desk, a chair, a balcony, and a view of the outdoors.

10. Best Western Indian Oak

Best Western Indian Oak
Chesterton
  • Serene lakeside luxury with spectacular views, indoor pool, and sauna near Indiana Dunes National Park.
￥13,416
￥15,026 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Indian Oak
View all properties

Top Chesterton Hotel Reviews

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
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

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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