A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25
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 window, a desk, 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 fireplace, and a television.

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

Full House booking of a history building close to the Dunes
Chesterton
￥282,108
￥360,997 total
includes taxes & fees
Oct 26 - Oct 27
Full House booking of a history building close to the 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 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.

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
￥31,504
￥39,894 total
includes taxes & fees
Oct 13 - Oct 14
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A large house surrounded by dense forest with a beach and ocean in the background.
A corner room with two wicker chairs, a small table, and a bay window with a view of trees.
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.

3. Furness Mansion

Furness Mansion
Chesterton
￥21,016
￥23,538 total
includes taxes & fees
Oct 13 - Oct 14
Furness Mansion
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 bedroom with a bed, a nightstand, a ceiling fan, a window with curtains, and a view of greenery outside.
A modern kitchen with a central island, stainless steel appliances, and a clock on the wall.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,171
￥61,880 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
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 spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥17,012
￥19,054 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Chesterton
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
￥20,422
￥26,419 total
includes taxes & fees
Oct 19 - Oct 20
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A bathroom with a toilet, sink, and shower.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.
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
￥18,839
￥24,646 total
includes taxes & fees
Oct 13 - Oct 14
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
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.

8. Spring House Inn

Spring House Inn
Chesterton
￥15,673
￥18,346 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A reception area with a counter, a vending machine, and a view of the outside through glass doors.
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.
A modern kitchen with a coffee station, a bread display, and a refrigerated display.

9. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
Chesterton
￥14,837
￥16,616 total
includes taxes & fees
Nov 3 - Nov 4
Comfort Inn & Suites Porter near Indiana Dunes
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.

10. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Lakeside luxury thrives at this Chesterton retreat where private balconies frame serene water views and wildlife encounters.
￥14,880
￥16,666 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
View all properties

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"It’s very dated. Casino floor had a lot of out of service machines. Ceiling paint was peeling and needs attention. Lack of available luggage carts. The latter needs to be remedied asap! William d’s was awesome!"
Michael 1-night trip
Posted 5 hours ago
Blue Chip Casino Hotel and Spa
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 4 days ago
Quality Inn Chesterton near Indiana Dunes National Park I-94
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"Extremely nice staff. Most comfortable bed. Breakfast was several steps above most hotels. Different items each day, and warm cinnamon rolls. We used the guest laundry too, which was super convenient. Will definitely stay again!"
Michele 3-night trip
Posted 6 days ago
Holiday Inn Express & Suites New Buffalo by IHG

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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