A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Chesterton luxury hotels

A brick building with a balcony and green shutters, surrounded by trees.

1. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,005 reviews)
"A nice, quiet retreat by the woods."
United States
Angela
The price is ￥14,329
￥16,837 total
includes taxes & fees
Nov 9 - Nov 10
Spring House Inn
A modern building with large windows and balconies, a wooden deck, and a calm lake.

2. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,005 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
The price is ￥14,090
￥15,781 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Indian Oak
A modern bathroom with a large mirror, a bathtub, and a sink.

3. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,000 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
The price is ￥14,840
￥16,621 total
includes taxes & fees
Nov 30 - Dec 1
Waterbird Lakeside Inn
A modern dining area with multiple tables and chairs, a kitchen area with blue cabinets, and a reception desk in the background.

4. Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
2.5 star property
Chesterton
7.8 out of 10, Good, (874 reviews)
"Had a great weekend. Staff was great, room was clean, facility was great for a budget."
United States
Albie
The price is ￥11,990
￥13,428 total
includes taxes & fees
Dec 3 - Dec 4
Quality Inn Chesterton near Indiana Dunes National Park I-94
A hotel lobby with a red carpet, a bookshelf with books, a potted plant, a table with chairs, a small table with a vase, and a door with a red mat.

5. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (397 reviews)
"Friendly staff great locatikn"
United States
Kayla
The price is ￥12,838
￥14,379 total
includes taxes & fees
Nov 5 - Nov 6
Fairbridge Inn Express Chesterton
A large house surrounded by dense forest with a beach and ocean in the background.

6. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (117 reviews)
"Staff was extremely helpful and responded promptly. The room was very clean, and inviting. Great location for the beaches or short trips to Michigan."
United States
Bryan
The price is ￥19,912
￥22,302 total
includes taxes & fees
Nov 11 - Nov 12
Furness Mansion
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

7. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,006 reviews)
"Excellent hotel, friendly staff"
United States
Cheryl
The price is ￥18,895
￥21,163 total
includes taxes & fees
Dec 4 - Dec 5
Hilton Garden Inn Chesterton
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

8. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
7.8 out of 10, Good, (1,000 reviews)
"Good one night stay. Nice to have breakfast there before we headed out."
United States
Julie Van
The price is ￥13,888
￥15,554 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn & Suites Porter near Indiana Dunes
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

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

8/10 Good
"Overall cleanliness, the elevator made sounds that were questionable. Staff friendly and professional. No hotel garage"
samantha 1-night trip
Posted 16 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

10/10 Excellent
"Had a great weekend. Staff was great, room was clean, facility was great for a budget."
Albie 2-night trip
Posted 1 day 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.