Title: Chesterton Cottages from CA $422 | 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 In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterton cottages ![Property grounds](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/821f9ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/50024efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/61b2e0c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/3fc4887d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treehouse Bungalow- Quaint and Cozy Getaway! [](https://www.expedia.ca/Michigan-City-Hotels-Treehouse-Bungalow-Quaint-And-Cozy-Getaway.h75766752.Hotel-Information) Michigan City 8.6/10 Excellent (55 reviews) "Great property and everything was as described. Easy check in process! Would only add to get some newer pillows as they are all extremely flat for the beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mehnaz S. CA $244 CA $651 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Michigan-City-Hotels-Treehouse-Bungalow-Quaint-And-Cozy-Getaway.h75766752.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/eb541ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/90-6159383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/12cdda7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/3019420f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Beach Steps to the Beach. [](https://www.expedia.ca/Union-Pier-Hotels-Private-Beach.h34512802.Hotel-Information) Union Pier 10/10 Exceptional (93 reviews) "Great stay for a week by the beach with family! Perfect location to walk right down to the beach each day. Excited to come back one day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jalen W. CA $750 CA $1,495 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Union-Pier-Hotels-Private-Beach.h34512802.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/9d8c9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/2bb9dc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/7213bc8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/c7069d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Cottage Walkable to All Downtown Michigan City & Beach! [](https://www.expedia.ca/Michigan-City-Hotels-Brand-New-Cottage-Walkable-To-All-Downtown-Michigan-City-Beach.h112733347.Hotel-Information) Michigan City 9.8/10 Exceptional (16 reviews) "Cute place, extremely clean, comfortable and well-outfitted. It's very convenient, with easy parking and great proximity to downtown Michigan City. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather O. CA $160 CA $422 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Michigan-City-Hotels-Brand-New-Cottage-Walkable-To-All-Downtown-Michigan-City-Beach.h112733347.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120730000/120728500/120728476/6463eaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120730000/120728500/120728476/147b9215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120730000/120728500/120728476/128ed23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120730000/120728500/120728476/63bfb585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3BR New Buffalo cottage - steps to downtown, Stray Dog, Beach - pets ok [](https://www.expedia.ca/New-Buffalo-Hotels-Charming-3-Bedroom-Cottage-New-Buffalo-Walk-To-Downtown-And-Beach-Pets-Allowed.h120728476.Hotel-Information) Downtown New Buffalo CA $258 CA $597 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/New-Buffalo-Hotels-Charming-3-Bedroom-Cottage-New-Buffalo-Walk-To-Downtown-And-Beach-Pets-Allowed.h120728476.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/86f9ac27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/4fa27233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/1e906a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/402dc28a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach! [](https://www.expedia.ca/New-Buffalo-Hotels-Secluded-Retreat.h113612419.Hotel-Information) New Buffalo 10/10 Exceptional (23 reviews) "great time had by all" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elliot S. CA $540 CA $618 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/New-Buffalo-Hotels-Secluded-Retreat.h113612419.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=2026-03-14&endDate=2026-03-15®ionId=7214&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America®ionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VILLA) ![](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-Cottages.d7214-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterton-Cottages.d7214-aaCottages.Travel-Guide-Accommodation) ## Top Chesterton Hotel Reviews ![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 "The room was very clean. Great staff! Quiet area. Good location." [](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 "Clean room, great amenities, super friendly staff, and good food. Perfect stop for the night. " [](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 "first a asked for a upgrade and they gave me one the room was absolutely beautiful and spotless; the staff was really really good i will return" [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.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 "Everything there was great. Had a really good time. " [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Holiday Inn Express & Suites New Buffalo by IHG](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/7a2e1c74_y.jpg) ### Holiday Inn Express & Suites New Buffalo by IHG 10/10 Excellent "Room very clean,hotel staff very pleasant and knowledgeable. Breakfast was hot." [](https://expedia.ca/Benton-Harbor-Hotels-Holiday-Inn-Express-Suites-New-Buffalo.h543985.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 "Wonderful home, gorgeous views, everything we needed for weekend. Exactly as described. " [](https://expedia.ca/Chesterton-Hotels-Cabin-53-Steps-From-Porter-Beach-On-Lake-Michigan-Family-Pet-Friendly.h96743172.Hotel-Information) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "This is a super cute Inn nestled in some woods. We were greeted by a family of deer right outside our room. Room was clean, quiet and affordable! Felt more like a State Park Inn. " [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg) ### Best Western Indian Oak 10/10 Excellent "Courteous service at check in , clean and comfy room stay, loved the lake view room !. " [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.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 " [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ## Find out more about Chesterton ## Chesterton Cottages information | Number of reviews | 132 | | ----------------- | ----------- | | Accommodation | 90 Cottages | | Lowest Price | CA $422 | | Highest Price | CA $1,495 | ## Frequently asked questions ### Why book your cottage in Chesterton with Expedia? ### How can I find cheap cottages in Chesterton? ### What is there to do in Chesterton near my cottage? ## 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) - 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