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) ![Lake Michigan. Path off Trail 9 at one place leads right to the lake. Peaceful to just stand and watch and listen to the waves as they crash to the shore. Trail 9 is the trail to hike if one wants to see the most in the shortest time. Great views throughout the trail. The trail is over 3 miles long and is considered a moderate trail. But certainly worth it. One gets to hike through forest, dunes, and other natural environments and see such a variety of sights. #hiking](https://images.trvl-media.com/place/6091455/985eab23-71e6-415a-af69-65e5707ce659.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ruslian # Find luxury hotels in Chesterton, IN - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-27&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-28&endDate=2025-12-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for 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) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/e7c5dde3.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/3000000/2450000/2450000/2449990/92f96ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterbird Lakeside Inn [](https://www.expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) Chesterton 8.2/10 Very good (990) "Balcony was a nice extra. Room was clean and bed was comfortable. I’d stay here again if in the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorge [](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) ![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) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/d1f80e61.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) ### Quality Inn Chesterton near Indiana Dunes National Park I-94 [](https://www.expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) Chesterton 8.0/10 Very good (719) "Good stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Taesung CA $106 CA $119 total includes taxes & fees Jan 14 - Jan 15, 2026 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/527d397d.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) ![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 [](https://www.expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) Chesterton 8.6/10 Excellent (1001) "The room's clean and comfy, the staff super helpful, thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dmytro CA $128 CA $143 total includes taxes & fees Jan 2 - Jan 3, 2026 [](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=2026-01-10&endDate=2026-01-11®ionId=7214&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg) ### Best Western Indian Oak 10/10 Excellent "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 they were still comfy. Was a stain on our comforter that almost looked like baby food could have been spilt but no other complaints. Will stay again if we ever need to come back this way. View was also really nice of the water. " [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg) ### Ameristar Casino Hotel East Chicago 10/10 Excellent "Very clean" [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Quality Inn Chesterton near Indiana Dunes National Park I-94](https://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 "Good stay" [](https://expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) ![Blue Chip Casino Hotel and Spa](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg) ### Blue Chip Casino Hotel and Spa 10/10 Excellent "Good value and clean room" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "We had a plumbing problem and it was immediately fixed. We were swapped rooms so that it wouldnt interfere with our plans. Comfortable beds and a beautiful view of the lake. " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Baymont by Wyndham New Buffalo](https://images.trvl-media.com/lodging/1000000/870000/867300/867230/6dac1343_y.jpg) ### Baymont by Wyndham New Buffalo 10/10 Excellent "Staff was friendly. Room was clean. Breakfast was nothing to brag about. Also the pool and hot tub are both out of order at the time which was disappointing bc it was one of the reasons we booked this hotel. They do have a jacuzzi room, which was what we booked thankfully and that was nice and worked properly. " [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ## Frequently asked questions ### Which area of Chesterton is best to stay in for luxury hotels? > This central part of Chesterton offers a selection of quality accommodation options, often within walking distance of local eateries, independent shops, and the Chesterton European Market, which is held on Saturdays. The architecture here blends historic buildings with newer developments, creating a pleasant town centre feel. > > > Couples looking for a refined getaway will find downtown Chesterton appealing. They can enjoy leisurely strolls to nearby restaurants for dinner, explore the local boutiques, and easily access the Indiana Dunes National Park for daytime excursions. ### How much does a luxury hotel in Chesterton cost? ### What luxury activities and experiences are there in Chesterton? > For those prioritising access to nature and outdoor activities, staying near the Indiana Dunes National Park entrance is ideal. Hotels in this vicinity typically offer easy access to hiking trails, the expansive Lake Michigan shoreline, and opportunities for birdwatching. This area is great for active couples or solo travellers who appreciate being close to natural landscapes and want to spend their days exploring the outdoors. > > > If you prefer to be closer to local dining and shopping, the Chesterton town centre provides a pleasant base. The main street, Broadway, features a selection of independent shops, local eateries, and the Chesterton European Market on Saturdays during warmer months. This area is well-suited for couples who enjoy a leisurely pace, with options for an evening stroll and a nice meal without needing to travel far. ### How can I save on a luxury hotel in Chesterton with Expedia? ### Is it cheaper to book a luxury Chesterton hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## 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) - 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