Title: Chesterton Guest Houses from CA $292 | 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 # Search Guest Houses in Chesterton from CA $292 - ![](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 [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Our top choices for Chesterton guest houses ![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) ![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 9.2/10 Wonderful (14) "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 $274 CA $548 total includes taxes & fees Jan 2 - Jan 3 [](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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118130000/118121300/118121229/c6f6ed55.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) ### Beacons' Nest – Valpo U, Downtown & Dunes [](https://www.expedia.ca/Valparaiso-Hotels-Beacons-Nest-Valpo-U.h118121229.Hotel-Information) Valparaiso 10/10 Exceptional (2) "I stayed at the Beacon’s Nest for about 3 weeks, with my family coming in and out. It is a comfortable spot, perfectly sized for up to 4 people. It’s just minutes from downtown Valdosta with shops and restaurants.I have no complaints about the property at all as it served us well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra B. CA $96 CA $341 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Valparaiso-Hotels-Beacons-Nest-Valpo-U.h118121229.Hotel-Information) ![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) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829715/f85ac14a.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 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-Triple-Room.h117829715.Hotel-Information) 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 $390 CA $475 total includes taxes & fees Jan 3 - Jan 4 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-Triple-Room.h117829715.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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829724/405ffb32.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) ### Galien Room Suite King size with Jacuzzi [](https://www.expedia.ca/New-Buffalo-Hotels-Deluxe-Suite.h117829724.Hotel-Information) Downtown New Buffalo CA $336 CA $410 total includes taxes & fees Jan 3 - Jan 4 [](https://www.expedia.ca/New-Buffalo-Hotels-Deluxe-Suite.h117829724.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 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-King-Room.h117829728.Hotel-Information) Downtown New Buffalo CA $240 CA $292 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/New-Buffalo-Hotels-Superior-King-Room.h117829728.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) ![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) ![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) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117830000/117829800/117829711/60811176.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 $336 CA $409 total includes taxes & fees Jan 3 - Jan 4 [](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=2026-01-15&endDate=2026-01-16®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 ![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 "First time there and honestly thoroughly impressed from the parking garage convenience to the room cleanliness. Without a doubt will be back." [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.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 "🤘" [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Hilton Garden Inn Chesterton](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/87c7ddbf_y.jpg) ### Hilton Garden Inn Chesterton 10/10 Excellent "Amazing! Very clean, comfortable and great service for the reasonable price. Hotel bar food and drinks were good and the staff was very friendly!" [](https://expedia.ca/Chesterton-Hotels-Hilton-Garden-Inn-Chesterton.h858225.Hotel-Information) ![Extended Stay America Suites Merrillville US Rte 30](https://images.trvl-media.com/lodging/1000000/50000/40900/40847/cf9b8ed3_y.jpg) ### Extended Stay America Suites Merrillville US Rte 30 10/10 Excellent "Clean and quiet room, helpful and friendly staff." [](https://expedia.ca/Merrillville-Hotels-Extended-Stay-America-Suites-Merrillville-US-Rte-30.h40847.Hotel-Information) ![Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly](https://images.trvl-media.com/lodging/97000000/96750000/96743200/96743172/48dc1df9_y.jpg) ### Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly 10/10 Excellent "I don’t know what to say other than it’s a great property! Excellent view of the beach and lake. We walked on the beach all the days even tho it’s December. Everything you need is supplied. It’s clean and fully functional. Our family, including our pups, really enjoyed it there! Would definitely stay again. " [](https://expedia.ca/Chesterton-Hotels-Cabin-53-Steps-From-Porter-Beach-On-Lake-Michigan-Family-Pet-Friendly.h96743172.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) ![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 "Check in was easy ans convenient " [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "cleanliness, amenities, kind staff" [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.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 "Excellent service " [](https://expedia.ca/Merrillville-Hotels-FairBridge-Inn-Express-Merrillville.h123860.Hotel-Information) ## Find out more about Chesterton ## Chesterton Guest Houses information | Number of reviews | 17 | | ----------------- | --------------- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $292 | | Highest Price | CA $548 | ## Explore a world of travel with Expedia - 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