A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
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 ceiling fan, a fireplace, and a television.
A bedroom with a bed, a ceiling fan, a window, a desk, and a chair.
A bedroom with a bed, a desk, a chair, a television, and a ceiling fan.

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 12 - Oct 13
Full House booking of a history building close to the Dunes
A hot tub with a view of a swimming pool and a fenced garden area.
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 two-story building with a white exterior and a covered porch.

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
Nov 2 - Nov 3
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 bar area with multiple seating options, including bar stools and round tables with chairs.
A modern reception area with a wooden reception desk, a small seating area, and a snack bar with various packaged goods.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥20,839
￥23,339 total
includes taxes & fees
Nov 1 - Nov 2
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 modern kitchen with a central island, stainless steel appliances, and a clock on the wall.
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.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,098
￥62,231 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
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
Tower Haus w/Private Hot Tub
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.

6. Furness Mansion

Furness Mansion
Chesterton
￥19,488
￥21,827 total
includes taxes & fees
Oct 8 - Oct 9
Furness Mansion
A beach with sand dunes and grass.
A wooden play structure with a slide and a small building.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.
A wooden bridge in a forested area.

7. 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 7 - Oct 8
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A beach with a parking lot and buildings in the background.
A dining area with a table set for four, a potted plant, and a kitchen in the background.
A bedroom with a bed, bedside tables, a nightstand, a window, and a bathroom with a bathtub.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.

8. 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 7 - Oct 8
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 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 wooden deck with two white plastic chairs facing a calm lake and forested hills.

9. 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 brick building with a balcony and green shutters, surrounded by trees.
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.
A pool area with a round table and chairs, a tiled floor, and large windows.

10. Spring House Inn

Spring House Inn
Chesterton
￥11,720
￥13,915 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
View all properties

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Everything was great! Staff is very nice!"
David 1-night trip
Posted 11 hours ago
Blue Chip Casino Hotel and Spa
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"The room was spacious, extremely clean and had a beautiful bathroom. Great parking and professional front desk staff. Would give 5 stars except for the fact it smelled like weed in several places throughout the hotel, unfortunately."
Joane 1-night trip
Posted 17 hours ago
Ameristar Casino Hotel East Chicago
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 7 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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