Title: Chesterton Condo Rentals from CA $299 | 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 condo rentals ![Property grounds](https://images.trvl-media.com/lodging/107000000/106820000/106817100/106817023/f4888194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106820000/106817100/106817023/7a707bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106820000/106817100/106817023/78f8c96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/107000000/106820000/106817100/106817023/02fb5156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Valparaiso [](https://www.expedia.ca/Valparaiso-Hotels-Lake-Retreat-With-Unique-Dome-Near-Indiana-Dunes.h106817023.Hotel-Information) 10/10 Exceptional (4 reviews) "My partner and I stayed here for two nights and had a phenomenal time. The hot tub was ready to go and the perfect temperature, the dome was absolutely delightful for a peaceful afternoon reading and enjoying a glass of wine, the fireplace inside was a cozy setting for a competitive game of Uno, the bed was very comfortable, and everything was clean, modern, and exactly as pictured. I would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate L. CA $259 CA $328 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Valparaiso-Hotels-Lake-Retreat-With-Unique-Dome-Near-Indiana-Dunes.h106817023.Hotel-Information) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/0226147a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/583d104b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/183e6efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/92dc4cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Portage [](https://www.expedia.ca/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information) 9.6/10 Exceptional (12 reviews) "Very nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LeAnna M. CA $244 CA $311 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/d99ed1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/71f507ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/28334f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/15ebf54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Schererville [](https://www.expedia.ca/Schererville-Hotels-Free-Breakfast-Indoor-Pool-Gym-Business-Center.h82999916.Hotel-Information) CA $233 CA $299 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Schererville-Hotels-Free-Breakfast-Indoor-Pool-Gym-Business-Center.h82999916.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/b3be6fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/c59160d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/b4610d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/5099ab10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Schererville [](https://www.expedia.ca/Schererville-Hotels-King-Bed-Suite-Indoor-Pool-Free-Breakfast.h86147480.Hotel-Information) CA $422 CA $541 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Schererville-Hotels-King-Bed-Suite-Indoor-Pool-Free-Breakfast.h86147480.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/4af11984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/8b5408c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/b63f36bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/e2fa30cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Schererville [](https://www.expedia.ca/Schererville-Hotels-2-Bedroom-Free-Daily-Breakfast-Indoor-Pool.h88274464.Hotel-Information) CA $390 CA $496 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Schererville-Hotels-2-Bedroom-Free-Daily-Breakfast-Indoor-Pool.h88274464.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=2026-03-11&endDate=2026-03-12®ionId=7214&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APARTMENT) 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=COTTAGE) 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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-Condos.d7214-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterton-Condos.d7214-aaCondos.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 "Everything there was great. Had a really good time. " [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.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 "Room was amazing " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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) ![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 "Great area and staff was attentive " [](https://expedia.ca/Benton-Harbor-Hotels-Holiday-Inn-Express-Suites-New-Buffalo.h543985.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 "The room was very clean, and comfortable. We had a great time even though we couldn’t stay as long as we wanted cause life is living. There was no free breakfast " [](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 "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) ![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 "Nice Stay. " [](https://expedia.ca/Hammond-Hotels-Fairfield-Inn-Suites-By-Marriott-Chicago-SoutheastHammond.h62954.Hotel-Information) ## Find out more about Chesterton ## Chesterton Condo Rentals information | Number of reviews | 4 | | ----------------- | ---------------- | | Accommodation | 28 Condo Rentals | | Lowest Price | CA $299 | | Highest Price | CA $541 | ## Frequently asked questions ### Why book your condo in Chesterton with Expedia? ### How can I find cheap condos in Chesterton? ### What is there to do in Chesterton near my condo? ## 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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