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 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
￥281,396
￥360,086 total
includes taxes & fees
Nov 2 - Nov 3
Full House booking of a history building close to the Dunes
A beach with sand dunes and grass.
A wooden play structure with a slide and a small building.
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.

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
￥31,424
￥39,793 total
includes taxes & fees
Oct 12 - Oct 13
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 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.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥21,142
￥23,680 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,108
￥61,724 total
includes taxes & fees
Nov 2 - Nov 3
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 bedroom with a bed, a desk, a chair, a TV, and a ceiling fan.
A dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.

5. Furness Mansion

Furness Mansion
Chesterton
￥19,496
￥21,836 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 wooden bridge in a forested area.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,370
￥26,352 total
includes taxes & fees
Oct 11 - Oct 12
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 living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.

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
￥18,791
￥24,583 total
includes taxes & fees
Oct 8 - Oct 9
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 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'.

8. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Lakeside luxury thrives at this Chesterton retreat where private balconies frame serene water views and wildlife encounters.
￥14,867
￥16,651 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.
A bedroom with a bed, two windows, a nightstand, and a patterned rug.
A living room with a flat-screen TV mounted on the wall, a sofa, a coffee table with books and a bottle, and a window with a view of the outside.

9. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
￥17,736
￥60,189 total
includes taxes & fees
Oct 18 - Oct 19
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | 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 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.

10. Spring House Inn

Spring House Inn
Chesterton
￥11,725
￥13,922 total
includes taxes & fees
Nov 2 - Nov 3
Spring House Inn
View all properties

Top Chesterton Hotel Reviews

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 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
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 8 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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