Title: Chesterton Guest Houses from CA $289 | 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 prices for these dates Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterton guest houses ![Beach nearby](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/3f529486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/147e5317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/d29eb5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/e83c4a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo [](https://www.expedia.ca/New-Buffalo-Hotels-Luxury-Guesthouse-In-Private-Wooded-Setting-In-Grand-Beach-New-Buffalo.h60170967.Hotel-Information) New Buffalo 8.4/10 Very good (16 reviews) "Cute area and perfect for a birthday weekend away with my husband! Everything was clean and cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel D. CA $272 CA $542 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/New-Buffalo-Hotels-Luxury-Guesthouse-In-Private-Wooded-Setting-In-Grand-Beach-New-Buffalo.h60170967.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/2017e180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/0edbace3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/14db09cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/b2f6734e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eber Knight Studio - King size with Jacuzzi [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-King-Room.h117829728.Hotel-Information) Downtown New Buffalo CA $238 CA $289 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-King-Room.h117829728.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/f85ac14a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/f818cdbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/d5e05f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/cf25576f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain Whittaker Suite 2 bedroom, 2 baths [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-Triple-Room.h117829715.Hotel-Information) Downtown New Buffalo 10/10 Exceptional (1 review) "Nice place to stay, Lisa was great to communicate with and very responsive. Close to all key attractions in town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad H. CA $388 CA $471 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-Triple-Room.h117829715.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/60811176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/a050c62f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/aad5bd66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/bd9ccc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SS Post Boy Queen Suite with Jacuzzi [](https://www.expedia.ca/New-Buffalo-Hotels-One-Bedroom-Suite.h117829711.Hotel-Information) Downtown New Buffalo CA $334 CA $407 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/New-Buffalo-Hotels-One-Bedroom-Suite.h117829711.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=2026-03-02&endDate=2026-03-03®ionId=7214&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&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=AA_SPRING_PROMO_7214) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChesterton-Guest-Houses.d7214-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterton-Guest-Houses.d7214-aaGuestHouses.Travel-Guide-Accommodation) ## 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 "The room had a cup half full of a clear liquid on the table, a room key card for room 1116 (my room number was 1112), also there was a receipt on the tv stand from apparently the prior guest, The hotel charged me a $10 booking fee that I wasn’t expecting and at checkout said they couldn’t print a receipt for me of my stay!" [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Four Winds Casino Resort – New Buffalo](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139_y.jpg) ### Four Winds Casino Resort – New Buffalo 10/10 Excellent "Very nice and clean 👌 " [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.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 "Very courteous service, room was perfect! Hot coffee and breakfast in morning. Highly recommend 👌 " [](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.Hotel-Information) ![FairBridge Inn Express Merrillville](https://images.trvl-media.com/lodging/1000000/130000/123900/123860/39572dda_y.jpg) ### FairBridge Inn Express Merrillville 10/10 Excellent "Clean rooms and a great staff " [](https://expedia.ca/Merrillville-Hotels-FairBridge-Inn-Express-Merrillville.h123860.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 "Yes room was perfect! " [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond](https://images.trvl-media.com/lodging/1000000/70000/63000/62954/61626b2d_y.jpg) ### Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond 10/10 Excellent "The staff was very accommodating, the room very clean and comfortable and the breakfast buffet was delicious! I will stay again." [](https://expedia.ca/Hammond-Hotels-Fairfield-Inn-Suites-By-Marriott-Chicago-SoutheastHammond.h62954.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 "Room clean, area quiet. Slept fine. Breakfast leaves a lottle to be desired though. The sausages and eggs didn't taste right. " [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Comfort Inn Hobart-Merrillville I-65](https://images.trvl-media.com/lodging/1000000/50000/42500/42459/d222dd8e_y.jpg) ### Comfort Inn Hobart-Merrillville I-65 10/10 Excellent "Room was clean and staff was friendly." [](https://expedia.ca/Hobart-Hotels-Comfort-Inn-Hobart-Merrillville.h42459.Hotel-Information) ![Motel 6 Hammond, IN - Chicago Area](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037771/171cde49_y.jpg) ### Motel 6 Hammond, IN - Chicago Area 10/10 Excellent "Yes" [](https://expedia.ca/Hammond-Hotels-Motel-6-Hammond.h1037771.Hotel-Information) ## Find out more about Chesterton ## Chesterton Guest Houses information | Number of reviews | 17 | | ----------------- | --------------- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $289 | | Highest Price | CA $542 | ## 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) - 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