Title: Book the Best Chesterton LUXURY Hotels - Upscale Hotels in Chesterton, IN | Expedia.ca [Hotels in Chesterton](https://expedia.ca/Chesterton-Hotels.d7214.Travel-Guide-Hotels)[Vacation Rentals in Chesterton](https://expedia.ca/Chesterton-Vacation-Rentals.d7214.Travel-Guide-VacationRentals)[Things to do in Chesterton](https://expedia.ca/Things-To-Do-In-Chesterton.d7214.Travel-Guide-Activities)[Chesterton Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterton.d7214.Car-Rental-Guide)[Chesterton Vacation Packages](https://expedia.ca/Chesterton.d7214.Destination-Travel-Guides) ![Indiana Dunes State Park showing general coastal views and a beach as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/232000/232034-Indiana-Dunes-State-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Chesterton, IN ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chesterton Luxury Hotels Tonight [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-09-24&endDate=2025-09-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-09-25&endDate=2025-09-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterton Luxury Hotels ![Room, Lake View](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/d5680269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/d8936106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/92f96ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterbird Lakeside Inn Chesterton 8.2/10 Very good (948) "Average place but the location on the lake and balcony put it above the hotels on the highway!" CA $135 CA $152 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/be1c7179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/d0344802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/6fa344e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/ceddc266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Chesterton near Indiana Dunes National Park I-94 Chesterton 8.0/10 Very good (690) "Nice rooms comfy beds" CA $128 CA $144 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/77291ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/527d397d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/ddafc438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Indian Oak Chesterton 8.6/10 Excellent (1013) "Clean, Friendly staff, nice area" CA $141 CA $158 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-09&endDate=2025-10-10®ionId=7214&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![Best Western Indian Oak](//images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg) ### Best Western Indian Oak 10/10 Excellent "Breakfast was great, pool very clean. Rooms very clean. Everything very clean. " [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![Baymont by Wyndham New Buffalo](//images.trvl-media.com/lodging/1000000/870000/867300/867230/6dac1343_y.jpg) ### Baymont by Wyndham New Buffalo 10/10 Excellent "We have stayed here several times. The staff is always friendly and helpful. We will definitely be back." [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Blue Chip Casino Hotel and Spa](//images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg) ### Blue Chip Casino Hotel and Spa 10/10 Excellent "Clean Nice Place" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Ameristar Casino Hotel East Chicago](//images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg) ### Ameristar Casino Hotel East Chicago 10/10 Excellent "I love the valet parking and rooms." [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Waterbird Lakeside Inn](//images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "We liked the hospitality. Very nice hostess at the front. Room was okay. Comfy bed. The area surrounding the outside walk up needs updates and fixes. The room inside needs updates for more modern tastes. The batbroom cabinet was broken and wouldn't close completely" [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Quality Inn Chesterton near Indiana Dunes National Park I-94](//images.trvl-media.com/lodging/1000000/440000/439900/439829/be1c7179_y.jpg) ### Quality Inn Chesterton near Indiana Dunes National Park I-94 10/10 Excellent "Stay was comfortable and quiet. Easy check in. Good breakfast. Surrounding city had several dinner options and seemed safe to walk or drive around. " [](https://expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) ## 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 Indiana Dunes National Park and 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 Indiana Dunes National Park, Lake Michigan, and Lustron House. If you have extra time while you're in the area, you might want to see Indiana Dunes Visitor Center and Bailly Homestead - American Indians and Fur Traders. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Farmstay in Beverly Shores](https://www.expedia.ca/Beverly-Shores-Agritourism.d3000435761-aaAgritourism.Travel-Guide-Accommodation) - [Apartments in Beverly Shores](https://www.expedia.ca/Beverly-Shores-Apartments.d3000435761-aaApartments.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Beverly Shores](https://www.expedia.ca/Beverly-Shores-Hotels-Beach-Hotel.0-0-d3000435761-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Beverly Shores](https://www.expedia.ca/Beverly-Shores-Hotels-Cheap-Hotels.0-0-d3000435761-tCheapHotels.Travel-Guide-Filter-Hotels) - [Beverly Shores Hotels](https://www.expedia.ca/Beverly-Shores-Hotels.d3000435761.Travel-Guide-Hotels) - [Burns Harbor Hotels](https://www.expedia.ca/Burns-Harbor-Hotels.d553248634983526861.Travel-Guide-Hotels) - 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