Title: Book the Best HISTORIC Hotels in Chesterton in 2025 | 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 Historic Hotels in Chesterton, IN from CA $426 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Chesterton Historic Hotels Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterton Historic Hotels ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/w904h683x60y0-f1101b3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/w902h683x61y0-9073ebeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/9e77a378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/w906h683x59y0-1a965489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Moroccan Hideaway Michigan City 10/10 Exceptional (2) "We had such a wonderful stay! The place was cute, beautifully decorated, and had everything we needed for a comfortable weekend. The location was perfect—right downtown and close to all the restaurants, shops, and activities we wanted to enjoy. The host was fantastic and very attentive, which made the whole experience even better. We’d definitely stay here again and highly recommend it!" CA $189 CA $481 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Michigan-City-Hotels-The-Moroccan-Hideaway.h119611330.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112740000/112738400/112738317/a050bc8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112740000/112738400/112738317/d4868a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112740000/112738400/112738317/8ea2325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112738400/112738317/b87faedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Designer Loft Within Walking Distance to Restaurants, Bars & Beach! Pet Friendly Michigan City 9.4/10 Exceptional (10) "Excellent property with amazing restaurants! This place exceeded our expectations. I would definitely recommend to anyone visiting Michigan City. " CA $188 CA $464 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Michigan-City-Hotels-Designer-Loft-Within-Walking-Distance-To-Restaurants.h112738317.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78760000/78758700/78758615/e8192fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78760000/78758700/78758615/3b4be089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78760000/78758700/78758615/c82e159c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78760000/78758700/78758615/2abd5198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino! Michigan City 9.8/10 Exceptional (32) "Amazing place that was close to so many things" CA $212 CA $505 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Michigan-City-Hotels-Uptown-Penthouse-On-Pine-By-Lake-Michigan.h78758615.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34470000/34466400/34466349/75f01572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34470000/34466400/34466349/3bef9c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34470000/34466400/34466349/05bcffd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/35000000/34470000/34466400/34466349/e3ef7b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Restored 1870 Victorian Home in Historic LaPorte, IN all for you.. La Porte 9.8/10 Exceptional (79) "Great property and a wonderful host!!" CA $339 CA $431 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/La-Porte-Hotels-Restored-1870-Victorian-Home-In-Historic-LaPorte.h34466349.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5008e2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/25d100a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/92c83993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5b736ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views Michigan City 9.6/10 Exceptional (73) "Good location to the beach. Property was small and dated but clean and provided what we needed for a short weekend. " CA $612 CA $711 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Michigan-City-Hotels-On-Lake-Shore-Drive.h68923845.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=2025-10-21&endDate=2025-10-22®ionId=7214&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![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 "Super easy check in and out" [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ## Frequently asked questions ### What can I expect on my historical trip to Chesterton? > You're already probably planning a visit to historically relevant sites during your trip to Chesterton. While you're here, you can visit the shops and beaches. You can also relish a trip to the restaurants during your stay. ### How many historical hotels will I find in Chesterton? > In Chesterton, you'll find 61 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the most important historical places and other sights to visit in Chesterton? > Chesterton is notable for landmarks like Lustron House, Bailly Homestead - American Indians and Fur Traders, and Chellberg Farm. Natural beauty is on display at Indiana Dunes National Park, Lake Michigan, and Indiana Dunes Visitor Center. A couple of additional sights to add to your agenda are Coffee Creek Watershed Conservancy Preserve and Indiana Dunes State Park. ### What is a historic hotel like in Chesterton? > When you choose a historic hotel, you'll sleep someplace that has an officially recognized historic designation. A castle, a palace or even a pub or an old police station can be considered a historic hotel as long as it has special significance. Traditional architecture and period features are typically found in the guestrooms or communal spaces of these historic hotels in Chesterton, bringing the history to life. ### What is the difference between a historic hotel and a heritage hotel? > You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The architecture and building of historic hotels tend to be what's most significant. For a heritage hotel, it's mainly the cultural value and how it inspired the community. ### Do historic hotels in Chesterton have modern facilities? > Hotel interiors feature the modern conveniences and safety features you might expect, but every effort is made to preserve treasured traditions and historic facades. WiFi, heating and air conditioning, updated bathroom facilities, and the amenities found at a contemporary hotel will be available in a historic hotel. Rest assured that when you choose a historic hotel in Chesterton, you won't be staying at a place that's uncomfortable or rundown. ## 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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