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 ![](https://images.trvl-media.com/place/6091455/985eab23-71e6-415a-af69-65e5707ce659.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 6 - Mar 7](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-06&endDate=2026-03-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Mar 7 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-07&endDate=2026-03-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-06&endDate=2026-03-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-13&endDate=2026-03-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Chesterton luxury hotels ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/addb149b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 restaurants, lunch served](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/19b8928a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/69c06567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/089fa31c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ameristar Casino Hotel East Chicago [](https://www.expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) East Chicago 8.6/10 Excellent (1,006 reviews) "Yes everything was excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $128 CA $160 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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=2026-03-20&endDate=2026-03-21®ionId=7214&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_7214) ## Top Chesterton Hotel Reviews ![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 "Yea" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Baymont by Wyndham New Buffalo](https://images.trvl-media.com/lodging/1000000/870000/867300/867230/b618e5a6_y.jpg) ### Baymont by Wyndham New Buffalo 4/10 Poor "everything was down and our mattress pad and sheets were stained" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Holiday Inn Express & Suites New Buffalo by IHG](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/adce6183_y.jpg) ### Holiday Inn Express & Suites New Buffalo by IHG 8/10 Good "Late check in. No issues. Clean room. Decent breakfast " [](https://expedia.ca/Benton-Harbor-Hotels-Holiday-Inn-Express-Suites-New-Buffalo.h543985.Hotel-Information) ![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/527d397d_y.jpg) ### Best Western Indian Oak 8/10 Good "The room was clean but had an off fishy odor when you first walk in" [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/5ad6abf3_y.jpg) ### Waterbird Lakeside Inn 2/10 Terrible "room smell no vending machines " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/addb149b_y.jpg) ### Ameristar Casino Hotel East Chicago 4/10 Poor "The room was out of date. Also, I placed in handicap room which did not request due to being over booked. " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Days Inn by Wyndham Portage/Indiana Dunes National Park](https://images.trvl-media.com/lodging/2000000/1230000/1226300/1226286/833bc04a_y.jpg) ### Days Inn by Wyndham Portage/Indiana Dunes National Park 10/10 Excellent "Staff was courteous and helpful. Room was clean and comfy. I would stay here again. " [](https://expedia.ca/Portage-Hotels-Days-Inn-By-Wyndham-Portage.h1226286.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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