Title: Book the Best HISTORIC Hotels in Chesterton in 2026 | 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 Historic Hotels in Chesterton, IN from CA $430 - ![](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 Historic Hotels Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-08&endDate=2025-12-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterton Historic Hotels ![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) ![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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78760000/78758700/78758615/ceee5287.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 (36) "Great stay The place was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa M. CA $173 CA $449 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Michigan-City-Hotels-Uptown-Penthouse-On-Pine-By-Lake-Michigan.h78758615.Hotel-Information) ![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) ![Living area](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/9e77a378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/120000000/119620000/119611400/119611330/w903h683x60y0-e543fd0a.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) ### The Moroccan Hideaway Michigan City 10/10 Exceptional (3) "Cute and cozy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irene D. CA $210 CA $508 total includes taxes & fees Dec 11 - Dec 12 [](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) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112738400/112738317/b87faedc.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) ### Designer Loft Within Walking Distance to Restaurants, Bars & Beach! Pet Friendly Michigan City 9.4/10 Exceptional (13) "Excellent property with amazing restaurants! This place exceeded our expectations. I would definitely recommend to anyone visiting Michigan City. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne CA $187 CA $460 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Michigan-City-Hotels-Designer-Loft-Within-Walking-Distance-To-Restaurants.h112738317.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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34470000/34466400/34466349/19ea8870.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) ![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) ### Restored 1870 Victorian Home in Historic LaPorte, IN all for you.. La Porte 9.8/10 Exceptional (82) "We enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ramona M. CA $336 CA $430 total includes taxes & fees Dec 11 - Dec 12 [](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) ![Interior](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5b736ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/83d65721.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) ### On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views Michigan City 9.6/10 Exceptional (77) "House was very clean and not too far from the beach. Loved sitting on the porch listening to the water. Will definitely be booking again next year. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca B. CA $607 CA $704 total includes taxes & fees Dec 11 - Dec 12 [](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=2025-12-23&endDate=2025-12-24®ionId=7214&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![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 "nothing to say about it. was very lovely " [](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? ### How many historical hotels will I find in Chesterton? ### What are the most important historical places and other sights to visit in Chesterton? ### What is a historic hotel like in Chesterton? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chesterton have modern facilities? ## Explore a world of travel with Expedia - 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