Title: Chesterton Cottages from CA $389 | 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 Chesterton Cottage Rentals from CA $389 - ![](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 [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterton Cottages ![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) ![Exterior detail](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/0de38273.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/113000000/112740000/112733400/112733347/16fb0b29.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) ### Brand New Cottage Walkable to All Downtown Michigan City & Beach! Michigan City 9.6/10 Exceptional (15) "Beautiful and feels like home! Great location too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle T. CA $133 CA $389 total includes taxes & fees Nov 29 - Nov 30 [](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/89000000/88970000/88964500/88964431/1900aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/89000000/88970000/88964500/88964431/w1134h755x18y1-3146ccda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88970000/88964500/88964431/73919d34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88970000/88964500/88964431/w1169h1167x0y3-445908a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk Michigan City 9.6/10 Exceptional (49) "Great space, fun neighborhood, and perfect location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric B. CA $251 CA $591 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Michigan-City-Hotels-Sweet-Inn-Coach-House-Near-Beautiful-Beach-On-Lake-Michigan-In-Beachwalk.h88964431.Hotel-Information) ![House (3 Bedrooms) | Floor plan](https://images.trvl-media.com/lodging/122000000/121670000/121666100/121666019/d9db0ee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Floor plan](https://images.trvl-media.com/lodging/122000000/121670000/121666100/121666019/a11be051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Floor plan](https://images.trvl-media.com/lodging/122000000/121670000/121666100/121666019/b31571b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Floor plan](https://images.trvl-media.com/lodging/122000000/121670000/121666100/121666019/703d87b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3BR Home Firepit & Grill Miller Beach CA $137 CA $499 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Gary-Hotels-Spacious-3BR-Home-Firepit-Grill.h121666019.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/821f9ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/76000000/75770000/75766800/75766752/d3d97fbe.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) ![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! Michigan City 8.6/10 Excellent (55) "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 $175 CA $575 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Michigan-City-Hotels-Treehouse-Bungalow-Quaint-And-Cozy-Getaway.h75766752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/73718cfe.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113620000/113612500/113612419/7864ba2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach! New Buffalo 10/10 Exceptional (22) "Very clean and comfortable. A very nice place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judi S. CA $617 CA $706 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/New-Buffalo-Hotels-Secluded-Retreat.h113612419.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/119000000/118260000/118252500/118252479/705fa890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Floor plan](https://images.trvl-media.com/lodging/119000000/118260000/118252500/118252479/558fe2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Floor plan](https://images.trvl-media.com/lodging/119000000/118260000/118252500/118252479/ef808a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Floor plan](https://images.trvl-media.com/lodging/119000000/118260000/118252500/118252479/eb0f8eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3BR House With Firepit & Grill, Near Beach Miller Beach 5.0/10 (2) "It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaitlyn CA $185 CA $483 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Gary-Hotels-Spacious-3BR-House-With-Firepit-Grill.h118252479.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=2025-12-12&endDate=2025-12-13®ionId=7214&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VACATION_HOME) 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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APART_HOTEL) 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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=COTTAGE) 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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&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 ![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 "Our room was clean and well appointed. The staff was very nice. " [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Fairfield Inn and Suites By Marriott Merrillville](https://images.trvl-media.com/lodging/1000000/10000/5300/5258/b28d063e_y.jpg) ### Fairfield Inn and Suites By Marriott Merrillville 10/10 Excellent "Great services " [](https://expedia.ca/Merrillville-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Merrillville.h5258.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 "The people were nice and the place was very clean " [](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.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 "Staff was great, clean rooms! " [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Tru By Hilton Merrillville](https://images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/f4f30336_y.jpg) ### Tru By Hilton Merrillville 10/10 Excellent "There are many hotels right in this area to select from, we're so glad we picked this hotel! Not only was it clean and front desk staff was kind and welcoming and the breakfast buffet was delicious, what makes this hotel stand out even more than those positives is Annette! Annette is the day-maker who was keeping the breakfast buffet up and running. She takes a minute to meet each of the guests, introducing herself and asking about you, offers to assist with any breakfast requests, all with the most fabulous and genuine smile! It truly felt like Annette and the front desk staff we encountered truly cared about our experience. Thank you!" [](https://expedia.ca/Merrillville-Hotels-Tru-By-Hilton-Merrillville.h100803423.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 "Yes" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.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 "Great spacious room" [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.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 "." [](https://expedia.ca/Hammond-Hotels-Motel-6-Hammond.h1037771.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 "Place is clean. Staff is nice. Pool and hot tube are amazing. We’ve stayed here multiple times. " [](https://expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ## Find out more about Chesterton ## Chesterton Cottages information | Number of reviews | 143 | | --- | --- | | Accommodation | 92 Cottages | | Lowest Price | CA $389 | | Highest Price | CA $706 | ## Frequently asked questions ### Why book your cottage in Chesterton with Expedia? > Booking a cottage in Chesterton is as simple as deciding on your travel dates and picking an ideal place for a vacation in the outdoors. From chic retreats to low-cost properties and cottages that have perks like a hot tub, Expedia has something for all styles and tastes. As for irresistible deals? We have them too! ### How can I find cheap cottages in Chesterton? > With Expedia's convenient filter tool, sourcing cheap cottages in Chesterton has never been easier. To discover properties that are very pocket friendly, narrow your search results by star rating, amenities and budget. ### What is there to do in Chesterton near my cottage? > Whatever you love to do, Chesterton has lots of things to keep you going. [Indiana Dunes State Park](https://www.expedia.ca/Indiana-Dunes-State-Park-Indiana.d6162867.Vacation-Attraction), [Dune Acres Beach](https://www.expedia.ca/Dune-Acres-Beach-Dune-Acres.d553248635983990330.Vacation-Attraction) and [Coffee Creek Watershed Conservancy Preserve](https://www.expedia.ca/Coffee-Creek-Watershed-Conservancy-Preserve-Chesterton.d553248621532658879.Vacation-Attraction) are on most travelers' to-do lists. Don't leave without exploring [Lustron House](https://www.expedia.ca/Lustron-House-Chesterton.d553248621532658880.Vacation-Attraction), [Chellberg Farm](https://www.expedia.ca/Chellberg-Farm-Porter.d553248635796044827.Vacation-Attraction) and [Cowles Bog Trailhead](https://www.expedia.ca/Cowles-Bog-Trailhead-Dune-Acres.d641529330049224704.Vacation-Attraction) either. 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