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Featured Chesterton Family Hotels
Best Western Indian Oak
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 breakfast and the pool in our reviews. ...
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Quality Inn Chesterton near Indiana Dunes National Park I-94
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 ...
Fairbridge Inn Express Chesterton
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 ...
Waterbird Lakeside Inn
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. ...
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
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 breakfast and the pool in our reviews. ...
8.4/10 Very Good! (1,002 reviews)
"location"
Reviewed on Jun 24, 2025
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Stay at this 3-star 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! (1,006 reviews)
"We loved staying here."
Reviewed on Jun 26, 2025
Waterbird Lakeside Inn
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! (854 reviews)
"Loved the room with deck overlooking the beautiful swans in the lake."
Reviewed on Jun 28, 2025
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
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 breakfast and the pool in our reviews. ...
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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 by Star Rating
More Hotel Options
- Hotels with Free Parking in Chesterton
- Hotels with a Pool in Chesterton
- Hotels with Hot Tubs in Chesterton
- Resorts & Hotels with Spas in Chesterton
- Beach Hotels in Chesterton
- Luxury Hotels in Chesterton
- Hotels with an Indoor Pool in Chesterton
- Pet-friendly Hotels in Chesterton
- Romantic Hotels in Chesterton
Top Points of Interests in Chesterton
- Hotels near Indiana Dunes National Park
- Hotels near Indiana Dunes State Park
- Hotels near Indiana Dunes Visitor Center
- Hotels near Bailly Homestead - American Indians and Fur Traders
- Hotels near Coffee Creek Watershed Conservancy Preserve
- Hotels near Lustron House
- Hotels near Chellberg Farm
- Hotels near Chesterton Art Center
- Hotels near Lake Michigan
- Hotels near Four Winds Casino New Buffalo
- Hotels near Blue Chip Casino
- Hotels near Hard Rock Casino Northern Indiana
- Hotels near New Buffalo Public Beach
- Hotels near Local
- Hotels near Ameristar Casino East Chicago
- Hotels near Deep River Water Park
Cities near Chesterton
- New Buffalo Hotels (20.84 mi)
- Michigan City Hotels (11 mi)
- Union Pier Hotels (24.34 mi)
- Merrillville Hotels (17.01 mi)
- Hammond Hotels (22.92 mi)
- La Porte Hotels (17.63 mi)
- Portage Hotels (5.73 mi)
- Gary Hotels (14.17 mi)
- Valparaiso Hotels (9.9 mi)
- Three Oaks Hotels (26.75 mi)
- Crown Point Hotels (20.52 mi)
- Munster Hotels (23.37 mi)
- Southwest Michigan Hotels (49.3 mi)
- Schererville Hotels (22.14 mi)
- Porter Hotels (1.43 mi)
- Long Beach Hotels (13.88 mi)
- Great Lakes Hotels (287.26 mi)
- East Chicago Hotels (20.53 mi)
- Western Michigan Hotels (109.66 mi)
- Beverly Shores Hotels (6.64 mi)
Car Rentals Near Chesterton
- Car rentals in New Buffalo
- Car rentals in Michigan City
- Car rentals in Union Pier
- Car rentals in Merrillville
- Car rentals in Hammond
- Car rentals in La Porte
- Car rentals in Portage
- Car rentals in Gary
- Car rentals in Valparaiso
- Car rentals in Three Oaks
- Car rentals in Crown Point
- Car rentals in Munster
- Car rentals in Southwest Michigan
- Car rentals in Schererville
- Car rentals in Porter
- Car rentals in Long Beach
Top Family Hotel Destinations
- Las Vegas Family Hotels
- Arcade Family Hotels
- Branson Family Hotels
- Biloxi Family Hotels
- Ocean City Family Hotels
- Orlando Family Hotels
- Buffalo Family Hotels
- Reno Family Hotels
- Colorado Springs Family Hotels
- Phoenix Family Hotels
- Niagara Falls Family Hotels
- New York Family Hotels
- Whistler Family Hotels
- Houston Family Hotels
- Fort Walton Beach Family Hotels
- Pensacola Beach Family Hotels
- Tampa Family Hotels
- Myrtle Beach Family Hotels
- Miami Beach Family Hotels
- Birmingham Family Hotels
Top Booked Hotels in Chesterton
- Best Western Indian Oak
- Quality Inn Chesterton near Indiana Dunes National Park I-94
- Comfort Inn & Suites Porter near Indiana Dunes
- Fairbridge Inn Express Chesterton
- Hilton Garden Inn Chesterton
- Blue Chip Casino Hotel and Spa
- Baymont by Wyndham Michigan City
- Fairfield Inn and Suites By Marriott Merrillville
- Ameristar Casino Hotel East Chicago
- Quality Inn Near Interstate I94
- Super 8 by Wyndham Merrillville
- Baymont by Wyndham New Buffalo
- Baymont by Wyndham Portage Indiana Dunes