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 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
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 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 large bed, two bedside tables, a ceiling fan, 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
￥282,108
￥360,997 total
includes taxes & fees
Oct 12 - Oct 13
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 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.

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 spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
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.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥20,900
￥23,408 total
includes taxes & fees
Nov 1 - Nov 2
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 compact kitchen with grey cabinets, a wooden countertop, and a coffee maker.

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,171
￥62,412 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 corner room with two wicker chairs, a small table, and a bay window with a view of trees.
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
￥18,704
￥20,949 total
includes taxes & fees
Oct 15 - Oct 16
Furness Mansion
A beach with sand dunes and grass.
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.
A wooden bridge in a forested area.

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 12 - Oct 13
The "Pool Barn Camper" w/Hot Tub 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 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.

7. Spring House Inn

Spring House Inn
Chesterton
￥15,673
￥18,346 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 bedroom with a bed, two windows, a nightstand, and a patterned rug.
A modern kitchen with a stainless steel refrigerator, a gas stove, and a coffee station with cups and a coffee maker.
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
￥18,465
￥61,106 total
includes taxes & fees
Oct 14 - Oct 15
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with a parking lot and buildings in the background.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.
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.

9. 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 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 a chandelier.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.

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

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"The room was big. It had a huge bathtub and a separate shower. The beds were comfortable too. They charge you for amenities and that is the gym, dining, and casino. They should pay you. The casino is very expensive to eat at and the food was just OK. If they had microwaves in the room, I'd say bring your own food but they don't. The staff in the hotel, dining/ casino are not very friendly."
Cindy 1-night trip
Posted 10 hours ago
Ameristar Casino Hotel East Chicago
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 days ago
Quality Inn Chesterton near Indiana Dunes National Park I-94
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Loved the balcony looking out on the small lake behind the hotel. The front desk clerk was nice. Updated bathrooms were nice ecxept ours would not stay closed & had to use a washcoth to hold to closed.Otherwise a very nice stay for going to Indiana Dunes State Park"
Karen 2-night trip
Posted 2 days ago
Best Western Indian Oak
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 4 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.

Explore a world of travel with Expedia