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Featured Chesterton Family Hotels

Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Best Western Indian Oak
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hilton Garden Inn Chesterton
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 out of 5
418 Council Road Chesterton IN
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Chesterton near Indiana Dunes National Park I-94
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr. Chesterton IN
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Fairbridge Inn Express Chesterton
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Waterbird Lakeside Inn
See all 1,396 properties in Chesterton
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.

Hotels with Pools in Chesterton

Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.4/10 Very Good! (1,000 reviews)
We we went to breakfast and the juice was out as well as the yogurt. Went to front desk, told them, and she immediately went and changed them out. Front desk was super friendly and even allowed us to swim longer than pool was open. Pillows are like the size of throw pillows lol which was odd but ...

Reviewed on Dec 23, 2025

Best Western Indian Oak
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,002 reviews)
Very clean room Staff friendly

Reviewed on Dec 7, 2025

Hilton Garden Inn Chesterton
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (992 reviews)
My room is nice & cozy.

Reviewed on Dec 31, 2025

Waterbird Lakeside Inn
See all 1,396 properties in Chesterton
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.

Hotels With Connecting Rooms in Chesterton

Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road Chesterton IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Best Western Indian Oak
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hilton Garden Inn Chesterton
See all 1,396 properties in Chesterton
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.