Title: Chesterton Guest Houses from CA $301 | 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) # Search Guest Houses in Chesterton from CA $301 - ![](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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterton Guest Houses ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/a93796a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/434feb65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/10a6509e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/6e2741ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain Whittaker Suite 2 bedroom, 2 baths Downtown New Buffalo 10/10 Exceptional (1) "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 $386 CA $473 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-Triple-Room.h117829715.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/62451359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/fefadb22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/61000000/60180000/60171000/60170967/57f4478c.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) ### Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo New Buffalo 9.0/10 Wonderful (12) "Owner was very attentive to any needs or questions we had during the stay. Would definitely book again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $281 CA $562 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/New-Buffalo-Hotels-Luxury-Guesthouse-In-Private-Wooded-Setting-In-Grand-Beach-New-Buffalo.h60170967.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118130000/118121300/118121229/36793d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/119000000/118130000/118121300/118121229/0b65e480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/119000000/118130000/118121300/118121229/ad375c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/119000000/118130000/118121300/118121229/e44d3e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beacons' Nest – Valpo U, Downtown & Dunes Valparaiso 10/10 Exceptional (2) "Everything was fantastic. Trains are a little shocking if you’re not prepared." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kylah b. CA $79 CA $324 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Valparaiso-Hotels-Beacons-Nest-Valpo-U.h118121229.Hotel-Information) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/5606e57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/e68c2dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/2017e180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829728/28590d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eber Knight Studio - King size with Jacuzzi Downtown New Buffalo CA $246 CA $301 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-King-Room.h117829728.Hotel-Information) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829724/1f8fe249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829724/30032664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829724/0d46a4ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829724/405ffb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Galien Room Suite King size with Jacuzzi Downtown New Buffalo CA $316 CA $385 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/New-Buffalo-Hotels-Deluxe-Suite.h117829724.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829720/02f8c6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829720/5ec90029.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/118000000/117830000/117829800/117829720/0ca0ebd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829720/5b6d35de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snug Harbor Suite - King with Jacuzzi Downtown New Buffalo CA $288 CA $353 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/New-Buffalo-Hotels-King-Room-Apt.h117829720.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/ffcd94e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/bc38281f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/df24cb81.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/fe1bc0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SS Post Boy Queen Suite with Jacuzzi Downtown New Buffalo CA $316 CA $385 total includes taxes & fees Nov 21 - Nov 22 [](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=2025-11-23&endDate=2025-11-24®ionId=7214&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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 ![Waterbird Lakeside Inn](//images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "The room was so clean and spacious. The view was spectacular! The color of the fall leaves, the refraction of the sun off the lake. Morning dew rolling across the lake. Extremely quiet,in November. A Zen two day retreat. Highly recommended! Mental vacations are a necessity." [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Four Winds Casino Resort – New Buffalo](//images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139_y.jpg) ### Four Winds Casino Resort – New Buffalo 10/10 Excellent "Beautiful property and not over crowded! Very friendly staff! " [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![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 "Love that you are able to get a snack so late at night! 😊" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Quality Inn Near Interstate I94](//images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg) ### Quality Inn Near Interstate I94 10/10 Excellent "Staff was friendly and the room was comfortable. Hot tub was hot! Just the way I like it." [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Baymont by Wyndham Michigan City](//images.trvl-media.com/lodging/1000000/30000/21300/21232/6321c49b_y.jpg) ### Baymont by Wyndham Michigan City 10/10 Excellent "The room is beautiful and clean, the staff is very friendly and helpful. moreover, it provides great sense of safety. definitely will book at this hotel again if i revisit the city" [](https://expedia.ca/Michigan-City-Hotels-Baymont-By-Wyndham-Michigan-City.h21232.Hotel-Information) ![Spring House Inn](//images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "This was the cutest place! The surrounding area is gorgeous! The swings and fire were absolutely lovely! " [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.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 "The room was perfect! Clean, spacious and overall very good! The employees also so nice! " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Fairbridge Inn Express Chesterton](//images.trvl-media.com/lodging/1000000/30000/23400/23363/9161abd0_y.jpg) ### Fairbridge Inn Express Chesterton 10/10 Excellent "Staff was amazing. Debbie was super friendly and helpful when I locked myself out." [](https://expedia.ca/Chesterton-Hotels-Fairbridge-Inn-Express-Chesterton.h23363.Hotel-Information) ![Tru By Hilton Merrillville](//images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/f4f30336_y.jpg) ### Tru By Hilton Merrillville 10/10 Excellent "This was my husband and I first time stay on your property and it was an AWESOME experience. From our check in to our check out everything was definitely on point!!! I can't remember the young lady that checked us in because I want you to know that she represented you very well. We will definitely be returning soon even if it's just a weekend getaway." [](https://expedia.ca/Merrillville-Hotels-Tru-By-Hilton-Merrillville.h100803423.Hotel-Information) ## Find out more about Chesterton ## Chesterton Guest Houses information | Number of reviews | 12 | | --- | --- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $301 | | Highest Price | CA $562 | ## 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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