A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
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
￥281,592
￥360,337 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 two-story building with a white exterior and a covered porch.
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.

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
￥31,446
￥39,821 total
includes taxes & fees
Oct 18 - Oct 19
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana 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 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.

3. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,125
￥61,767 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 corner room with two wicker chairs, a small table, and a bay window with a view of trees.

4. Furness Mansion

Furness Mansion
Chesterton
￥20,557
￥23,024 total
includes taxes & fees
Oct 20 - Oct 21
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 large house with a swimming pool, a covered patio, and a garage with multiple doors.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,385
￥26,371 total
includes taxes & fees
Nov 1 - Nov 2
The "Pool Barn Camper" w/Hot Tub 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 spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A modern bar area with multiple seating options, including bar stools and round tables with chairs.

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥16,983
￥19,021 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A beach with a sunset, waves, and sparse vegetation.
A bedroom with a bed, pillows, a ceiling fan, and a wardrobe.
A two-story building with a dark exterior, a front porch with wooden beams, and a small front yard with a gravel path.
An outdoor patio with a gray sofa set, a barbecue grill, and a hot tub.

7. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
￥19,768
￥44,972 total
includes taxes & fees
Nov 3 - Nov 4
Tower Haus w/Private Hot Tub
A beach with a parking lot and buildings 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.
A dining area with a table set for four, a potted plant, and a kitchen in the background.

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
￥18,804
￥24,600 total
includes taxes & fees
Oct 28 - Oct 29
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 pool area with a round table and chairs, a tiled floor, and large windows.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
A spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.

9. Spring House Inn

Spring House Inn
Chesterton
￥15,644
￥18,311 total
includes taxes & fees
Nov 10 - Nov 11
Spring House Inn
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 spacious lobby with a staircase, a reception desk, and large windows offering a view of the outside.

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.
￥14,852
￥16,634 total
includes taxes & fees
Nov 15 - Nov 16
Waterbird Lakeside Inn
View all properties

Top Chesterton Hotel Reviews

Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"It was clean, the beds were comfy. Overall it was a good value."
Michael 1-night trip
Posted 1 hour ago
Best Western Indian Oak
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 9 days ago
Quality Inn Chesterton near Indiana Dunes National Park I-94

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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