A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
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 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
￥282,162
￥361,066 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 large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden play structure with a slide and a small building.
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
￥31,510
￥39,902 total
includes taxes & fees
Oct 18 - Oct 19
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 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.
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
￥25,311
￥29,035 total
includes taxes & fees
Oct 22 - Oct 23
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
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 living room with two wicker chairs, a small table, and a grey sofa.
A bedroom with a bed, a desk, a chair, a TV, and a ceiling fan.

4. Furness Mansion

Furness Mansion
Chesterton
￥21,019
￥23,541 total
includes taxes & fees
Oct 15 - Oct 16
Furness Mansion
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.
A two-story house with a porch, a garage, and a wooded backdrop.
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.

5. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,176
￥61,892 total
includes taxes & fees
Nov 3 - Nov 4
NEW! Beautiful Riverfront Home on 10 Acres!
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 spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a dining area, a sofa, a TV, and a microwave.

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥17,036
￥19,080 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Chesterton
A beach with sand dunes and grass.
A wooden bridge in a forested area.
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.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,426
￥26,424 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 modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.
A dining area with a table set for four, a potted plant, and a kitchen in the background.

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
￥18,842
￥24,650 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 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
￥15,676
￥18,349 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 a chandelier.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.
A spacious lobby with a staircase, a reception desk, and large windows offering a view of the outside.

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.
￥14,882
￥16,668 total
includes taxes & fees
Oct 26 - Oct 27
Waterbird Lakeside 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
"The hotel is clean, comfortable, great location near I94 and good restaurants, serves a good breakfast."
Susan 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites New Buffalo by IHG
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Anytime my wife and I need a little weekend getaway, we are headed to the Blue Chip Casino. The vibe was great. The food at the steakhouse was delicious. The room was top notch."
Joel 1-night trip
Posted 22 hours ago
Blue Chip Casino Hotel and Spa
Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

10/10 Excellent
"I was skeptical at first but it was the nicest, cleanest and most comfortable room I have stay in yet. Love the ambiance the entire place gives. The lady that night was amazing and friendly."
Rowena 1-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Michigan City
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 6 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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