A wooden staircase ascending a sandy hill with sparse vegetation.

Find Luxury Hotels in Chesterton, IN

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Luxury Hotels

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
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 bed, a ceiling fan, a window, a desk, and a chair.
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
￥279,542
￥357,713 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 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
￥31,217
￥39,531 total
includes taxes & fees
Oct 26 - Oct 27
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A sandy beach path leading to the sea with grassy dunes on either side.
A bedroom with a bed, a nightstand, a dresser, a window with blinds, and a chair.
A living room with a grey sofa, two armchairs, a coffee table, and a rug. There are two lamps, a framed picture on the wall, and a window with curtains.
A kitchen with wooden flooring, a stove, cabinets, a sink, and a window with a view.

3. Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
￥30,127
￥34,871 total
includes taxes & fees
Nov 8 - Nov 9
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
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 compact kitchen with grey cabinets, a wooden countertop, and a coffee maker.
A bedroom with a bed, a nightstand, a ceiling fan, a window with curtains, and a view of greenery outside.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥24,942
￥61,317 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 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.

5. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥16,980
￥19,017 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A large house surrounded by dense forest with a beach and ocean in the background.
A dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.
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.

6. Furness Mansion

Furness Mansion
Chesterton
￥19,366
￥21,690 total
includes taxes & fees
Oct 26 - Oct 27
Furness Mansion
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 pool area with a round table and chairs, a tiled floor, and large windows.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.

7. Spring House Inn

Spring House Inn
Chesterton
￥15,530
￥18,178 total
includes taxes & fees
Nov 1 - Nov 2
Spring House 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 a stainless steel refrigerator, a gas stove, and a coffee station with cups and a coffee maker.
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.

8. 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
￥20,161
￥62,991 total
includes taxes & fees
Nov 5 - Nov 6
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with a sunset, waves, and sparse vegetation.
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.
A bedroom with a bed, pillows, a ceiling fan, and a wardrobe.

9. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
￥21,460
￥47,227 total
includes taxes & fees
Oct 26 - Oct 27
Tower Haus w/Private Hot Tub
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 spacious lobby with a staircase, a reception desk, and a chandelier.
A wooden deck with two white plastic chairs facing a calm lake and forested hills.

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.
￥14,744
￥16,513 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside Inn
View all properties

Top Chesterton Hotel Reviews

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
"Clean room with comfortable bed. Very spacious King room. Casino easily accessible. Restaurant on site with great food options. Covered parking garage. Good value for the price."
Bronwyn 1-night trip
Posted 8 hours ago
Ameristar Casino Hotel East Chicago
Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"I did not like the bed . My hips and back hurt. It was a good bed just not for me."
Tami 1-night trip
Posted 17 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"The room was very clean. We stayed 2 days. Enjoyed the breakfast. The staff was always nice!"
Joan 2-night trip
Posted 2 days 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 2 weeks 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.

Explore a world of travel with Expedia