A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
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 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
Full House booking of a history building close to the Dunes
A sandy beach path leading to the sea with grassy dunes on either side.
A kitchen with wooden flooring, a stove, cabinets, a sink, and a window with a view.
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 dining room with a round table and four chairs, a decorative wall clock, and a window with blinds.

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

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
￥29,946
￥34,865 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.

3. 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 large house surrounded by dense forest with a beach and ocean in the background.
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.
A living room with two wicker chairs, a small table, and a grey sofa.

4. Furness Mansion

Furness Mansion
Chesterton
￥19,575
￥21,924 total
includes taxes & fees
Nov 26 - Nov 27
Furness Mansion
A beach with a sunset, waves, and sparse vegetation.
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.
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.

5. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
￥21,460
￥47,227 total
includes taxes & fees
Oct 27 - Oct 28
Tower Haus w/Private Hot Tub
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.

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥16,722
￥18,729 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Chesterton
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.
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.
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.
A modern kitchen with a stainless steel refrigerator, a gas stove, and a coffee station with cups and a coffee maker.

7. 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 4 - Nov 5
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A beach with sand dunes and grass.
A wooden bridge in a forested area.
A wooden play structure with a slide and a small building.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,236
￥26,178 total
includes taxes & fees
Nov 8 - Nov 9
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A brick building with a balcony and green shutters, surrounded by trees.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.
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
￥15,530
￥18,178 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A beach with a parking lot and buildings in the background.
A dining area with a table set for four, a potted plant, and a kitchen 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.

10. 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
￥18,668
￥24,422 total
includes taxes & fees
Oct 27 - Oct 28
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
View all properties

Top Chesterton Hotel Reviews

Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Room was clean. Was in town for a wedding and it was close to the venue. Nice spot."
Julissa 2-night trip
Posted 6 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
"Nice stay; even though the hot tub wasn’t working properly."
Shawn 1-night trip
Posted 8 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"Beautiful room! No microwave and pool was out of service, but still charged a resort fee.. otherwise a great stay."
Olivia 1-night trip
Posted 10 hours ago
Blue Chip Casino Hotel and Spa
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.

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