A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
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 large bed, two bedside tables, a ceiling fan, and a chair.
A bedroom with a bed, a desk, a chair, a television, and a ceiling fan.
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
￥280,505
￥338,847 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 two-story house with a porch, a garage, and a wooded backdrop.
A compact kitchen with grey cabinets, a wooden countertop, and a coffee maker.
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
￥42,343
￥83,389 total
includes taxes & fees
Oct 22 - Oct 23
NEW! Beautiful Riverfront Home on 10 Acres!
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.

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
￥31,325
￥38,610 total
includes taxes & fees
Oct 4 - Oct 5
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 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.
A hotel room with a dining area, a sofa, a TV, and a microwave.

4. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥24,358
￥27,281 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Garden Inn Chesterton
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 hotel room with a large bed, a desk, a chair, a balcony, and a view of the outdoors.

5. Best Western Indian Oak

Best Western Indian Oak
Chesterton
  • Serene lakeside luxury with spectacular views, indoor pool, and sauna near Indiana Dunes National Park.
￥17,378
￥19,463 total
includes taxes & fees
Oct 6 - Oct 7
Best Western Indian Oak
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.

6. Furness Mansion

Furness Mansion
Chesterton
￥19,224
￥21,531 total
includes taxes & fees
Oct 8 - Oct 9
Furness Mansion
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 modern kitchen with a coffee station, a bread display, and a refrigerated display.
A hotel room with a large bed, a bedside table with a lamp, a bathroom with a bathtub, and a window with curtains.

7. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
￥16,637
￥18,633 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Porter near Indiana Dunes
A beach with sand dunes and grass.
A wooden bridge in a forested area.
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.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,306
￥26,269 total
includes taxes & fees
Sep 30 - Oct 1
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 cozy living room with a dark-colored sofa, a round coffee table, and a small side table.
A bedroom with a bed, a ceiling fan, two bedside lamps, a black rug, and wooden flooring.
A compact kitchen with white cabinets, a stainless steel refrigerator, a gas stove, and a window with blinds.

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
￥18,889
￥41,606 total
includes taxes & fees
Oct 1 - Oct 2
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
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 living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.
A bedroom with a bed, bedside tables, a nightstand, a window, and a bathroom with a bathtub.

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
￥18,732
￥24,506 total
includes taxes & fees
Sep 30 - Oct 1
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
View all properties

Top Chesterton Hotel Reviews

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 hours ago
Waterbird Lakeside Inn
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Property is great, very helpful front desk staff. It is a short (under 5 minute) drive away from the 'town' area of New Buffalo (and the beach). Don't take the Amtrak to get here like we did though, there are no Lyfts/Ubers. And there is no sidewalk to walk from the property to the town and beach."
Abhishek 2-night trip
Posted 21 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Clean room and clean casino had a great time"
Ashley 1-night trip
Posted 22 hours ago
Blue Chip Casino Hotel and Spa

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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