A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

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.

1. Full House booking of a history building close to the Dunes

Full House booking of a history building close to the Dunes
Chesterton
9.4 out of 10, Exceptional, (6 reviews)
The price is ￥280,647
￥359,127 total
includes taxes & fees
Nov 3 - Nov 4
Full House booking of a history building close to the Dunes
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.

2. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
The price is ￥25,041
￥61,560 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
A beach with a sunset, waves, and sparse vegetation.

3. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (38 reviews)
The price is ￥21,545
￥47,238 total
includes taxes & fees
Nov 9 - Nov 10
Tower Haus w/Private Hot Tub
A large house surrounded by dense forest with a beach and ocean in the background.

4. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (116 reviews)
The price is ￥19,653
￥22,012 total
includes taxes & fees
Nov 18 - Nov 19
Furness Mansion
A beach with sand dunes and grass.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.6 out of 10, Excellent, (23 reviews)
The price is ￥20,316
￥26,282 total
includes taxes & fees
Nov 8 - Nov 9
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,006 reviews)
The price is ￥16,014
￥17,935 total
includes taxes & fees
Nov 28 - Nov 29
Hilton Garden Inn Chesterton
A beach with a parking lot and buildings in the background.

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
8.8 out of 10, Excellent, (139 reviews)
The price is ￥18,741
￥24,518 total
includes taxes & fees
Oct 29 - Oct 30
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A brick building with a balcony and green shutters, surrounded by trees.

8. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,022 reviews)
The price is ￥15,592
￥18,250 total
includes taxes & fees
Nov 2 - Nov 3
Spring House Inn
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.

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
9.6 out of 10, Exceptional, (75 reviews)
The price is ￥18,029
￥60,408 total
includes taxes & fees
Nov 3 - Nov 4
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A modern bathroom with a large mirror, a bathtub, and a sink.

10. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Lakeside luxury thrives at this Chesterton retreat where private balconies frame serene water views and wildlife encounters.
The price is ￥14,802
￥16,578 total
includes taxes & fees
Oct 29 - Oct 30
Waterbird Lakeside Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterton Hotel Reviews

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"No issue at all will stay here again"
Melissa 2-night trip
Posted 2 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.