A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
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 fireplace, and a television.
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
￥281,699
￥360,473 total
includes taxes & fees
Oct 28 - Oct 29
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 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
￥31,458
￥39,836 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 modern kitchen with a central island, stainless steel appliances, and a clock on the wall.
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.

3. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,135
￥61,791 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 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 dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.

4. Furness Mansion

Furness Mansion
Chesterton
￥17,837
￥19,978 total
includes taxes & fees
Oct 28 - Oct 29
Furness Mansion
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 modern bar area with multiple seating options, including bar stools and round tables with chairs.
A hotel room with a dining area, a sofa, a TV, and a microwave.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥17,264
￥19,336 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Chesterton
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 two-story building with a dark exterior, a front porch with wooden beams, and a small front yard with a gravel path.

6. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
Tower Haus w/Private Hot Tub
A beach with sand dunes and grass.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.
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.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,392
￥26,380 total
includes taxes & fees
Oct 19 - Oct 20
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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 dining area with a table set for four, a potted plant, and a kitchen in the background.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

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
￥18,812
￥24,610 total
includes taxes & fees
Oct 22 - Oct 23
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 room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
A pool area with a round table and chairs, a tiled floor, and large windows.

9. Spring House Inn

Spring House Inn
Chesterton
￥15,650
￥18,318 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A modern bathroom with a large mirror, a bathtub, and a sink.
A spacious lobby with a staircase, a reception desk, and large windows offering a view of the outside.
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.

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.
￥14,858
￥16,641 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
View all properties

Top Chesterton Hotel Reviews

Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

8/10 Good
"Manager was very welcoming and polite"
Joseph 2-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Michigan City
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Good location, easy access and parking. Staff friendly and helpful. Room decent sized and breakfast decent. Only stayed one night as was passing though. Would stay again."
Steve 1-night trip
Posted 11 hours ago
Best Western Indian Oak
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The hotel is clean, comfortable, great location near I94 and good restaurants, serves a good breakfast."
Susan 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites New Buffalo by IHG
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 7 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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