Title: Book the Best ROMANTIC Hotels in Chesterton, IN from CA $76 - Chesterton Romantic Getaways | 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 Romantic Hotels Tonight [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-21&endDate=2026-01-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Chesterton romantic hotels ![Gift shop](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/a7566650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, dinner served](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/70c2b529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/da35c845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Winds Casino Resort – New Buffalo [](https://www.expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) New Buffalo 9.4/10 Exceptional (1,664 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin CA $116 CA $135 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/8049367a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/61001108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/cf4bd60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Chip Casino Hotel and Spa [](https://www.expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) Michigan City 8.2/10 Very good (1,921 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe [](https://www.expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/3d41c4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/9b1179f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Room, 1 King Bed, Mobility Accessible, Ground Floor](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/758fc52b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/bd911feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brewery Lodge Hotel [](https://www.expedia.ca/Michigan-City-Hotels-The-Brewery-Lodge-Hotel.h27490226.Hotel-Information) Michigan City 9.0/10 Wonderful (800 reviews) "Great quiet place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maciej [](https://www.expedia.ca/Michigan-City-Hotels-The-Brewery-Lodge-Hotel.h27490226.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/e5d5f9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/d581e567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/65586f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![49-inch LCD TV with satellite channels, TV, MP3 dock](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/c092e27a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Merrillville [](https://www.expedia.ca/Merrillville-Hotels-Home2-Suites-By-Hilton-Merrillville.h18946541.Hotel-Information) Merrillville 9.0/10 Wonderful (1,001 reviews) "The room was very clean, and breakfast was really good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald CA $129 CA $145 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Merrillville-Hotels-Home2-Suites-By-Hilton-Merrillville.h18946541.Hotel-Information) ![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) ![Free self parking](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/b5958a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/71dc5fcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/eb6189bb.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 (1,000 reviews) "Yes absolutely great 👍 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tarance CA $125 CA $156 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Children's pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/48d008e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/c6f9a492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible, Non Smoking | Television](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/3e98203b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/ac23b9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn [](https://www.expedia.ca/Portage-Hotels-Rodeway-Inn.h40472.Hotel-Information) Portage 7.0/10 Good (802 reviews) "Fixing the place and doing a great job Freindly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua CA $68 CA $76 total includes taxes & fees Feb 19 - Feb 20 [](https://www.expedia.ca/Portage-Hotels-Rodeway-Inn.h40472.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/0862da23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/13fc3db3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/91e03b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/4ef2a8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Lake Resort and Banquets [](https://www.expedia.ca/La-Porte-Hotels-Laporte-Hotel-And-Conference-Center.h41829276.Hotel-Information) La Porte 6.8/10 (592 reviews) "Great place would have rates higher is hot tub was working" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jack CA $123 CA $142 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/La-Porte-Hotels-Laporte-Hotel-And-Conference-Center.h41829276.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/10000/300/259/81070b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/300/259/b7c2081b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/300/259/2dfb8f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/300/259/85d647a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Michigan City Inn [](https://www.expedia.ca/Michigan-City-Hotels-Ramada-By-Wyndham-Michigan-City.h259.Hotel-Information) Michigan City 4.6/10 (1,000 reviews) "Good area to stay for Indiana Dunes or beach. Hotel needs some new carpet and paint and would be a great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $97 CA $109 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Michigan-City-Hotels-Ramada-By-Wyndham-Michigan-City.h259.Hotel-Information) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/87bdc0c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5008e2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views [](https://www.expedia.ca/Michigan-City-Hotels-On-Lake-Shore-Drive.h68923845.Hotel-Information) Michigan City 9.6/10 Exceptional (77 reviews) "We had a lovely stay - all five of us and our dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise S. CA $607 CA $705 total includes taxes & fees Feb 17 - Feb 18 [](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=2026-02-04&endDate=2026-02-05®ionId=7214&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "Staff really nice. Room clean and better than expected. Nice layout and large rooms. " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "I’ve been booking short stays here since 2016 and the quality of customer service, on-site accommodations (especially the sauna), and the beauty of the grounds have gotten better year by year. Looking forward to the next couple of years…" [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Quality Inn Near Interstate I94](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg) ### Quality Inn Near Interstate I94 10/10 Excellent "The evening desk manager, Destiny, went out of her way to ensure the guests had an opportunity to watch the Bears-Packers playoff game. Awesome.....thanks again Destiny." [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Country Inn & Suites by Radisson, Merrillville, IN](https://images.trvl-media.com/lodging/2000000/1360000/1353900/1353808/4d6bf4d2_y.jpg) ### Country Inn & Suites by Radisson, Merrillville, IN 10/10 Excellent "My room was beautiful and clean and spacious, wonderful service " [](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.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 "Yes absolutely great 👍 " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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 "The midnight count down/ balloon drop" [](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/1000000/870000/867300/867230/6dac1343_y.jpg) ### Baymont by Wyndham New Buffalo 10/10 Excellent "Great stay" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Comfort Inn & Suites Porter near Indiana Dunes](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb_y.jpg) ### Comfort Inn & Suites Porter near Indiana Dunes 10/10 Excellent "Great staff and hospitality! Everything was clean and tidy. " [](https://expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chesterton? ### When is the best time of year for a romantic getaway to Chesterton? ### What is there to do in Chesterton? ### What's the best way to get to Chesterton and around town during my romantic getaway? ## 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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