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 - ![](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 [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-05&endDate=2025-11-06&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-06&endDate=2025-11-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## 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 (976) "Average place but the location on the lake and balcony put it above the hotels on the highway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracey [](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) ![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) ![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 (705) "Good stay in general" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Portia CA $113 CA $126 total includes taxes & fees Dec 1 - Dec 2 [](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) ![Hypo-allergenic bedding, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/20a0d4e7.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 (1014) "Clean room nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vicki CA $131 CA $147 total includes taxes & fees Nov 11 - Nov 12 [](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=2025-11-19&endDate=2025-11-20®ionId=7214&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![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 "Very nice room. Staff was very friendly." [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.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 "Always a comfy stay" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Best Western Indian Oak](//images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg) ### Best Western Indian Oak 10/10 Excellent "Fantastic and friendly staff. Clean, nice hotel. " [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.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 "Great customer service and clean." [](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 "Loved the balcony overlooking the lake " [](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 "Clean room, comfortable bed" [](https://expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) ## Frequently asked questions ### Which area of Chesterton is best to stay in for luxury hotels? > The best area to stay in Chesterton for luxury hotels is the downtown area, particularly around Calumet Road and Broadway. > > > > 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? > Luxury hotel prices in Chesterton vary, but you can find a great deal from CA $126 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Chesterton? > The best areas to stay in Chesterton are generally near the Indiana Dunes National Park entrance or within the town centre itself, offering a blend of natural beauty and local conveniences. > > > > 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? > There are plenty of ways to save on a luxury hotel in Chesterton. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Chesterton hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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