Title: Book the Best Chesterton FAMILY FRIENDLY Hotels from CA $99 - Kid-Friendly Hotels in Chesterton, IN | 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 # Find Family Hotels in Chesterton, IN from CA $99 - ![](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 availability on Chesterton Family Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Chesterton family-friendly hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/87c7ddbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/w3840h2559x0y1-f5d82d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/a5cc015f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/67d32234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chesterton Chesterton 8.8/10 Excellent (1001) "We loved staying here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $143 CA $160 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chesterton-Hotels-Hilton-Garden-Inn-Chesterton.h858225.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/d10fa939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/af092bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/d9c5f358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Porter near Indiana Dunes Chesterton 8.0/10 Very good (1003) "My room was clean and comfortable. I would definitely stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn CA $129 CA $144 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/be1c7179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/6fa344e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/d0344802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/d1f80e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Chesterton near Indiana Dunes National Park I-94 Chesterton 8.0/10 Very good (717) "Clean room, easy check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Billy CA $106 CA $119 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h956x0y4-8321b274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h956x0y0-3aad212e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1435h950x0y4-962b42a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h955x0y5-c37c59a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes Chesterton 9.8/10 Exceptional (63) "This place was great. It was very spacious, clean, and close to restaurants and grocery stores. The host was very communicative and answered any questions we had very quickly. The house was easy to find and parking was right in front of the house. The neighborhood was quiet and safe." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine C. CA $107 CA $441 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chesterton-Hotels-Relaxing-3-Bedroom-I-2-Baths-I-2-Living-Rooms-Home.h89011067.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/w1024h495x0y94-e2667f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/10372699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/52539792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/9f313aa4_edited_b133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes Porter 8.8/10 Excellent (16) "Great place to stay with kids." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane H. CA $161 CA $211 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Chesterton-Hotels-The-Pool-Barn-WPool.h69385681.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/046bf033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/4a9c4df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/cacec885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/93a3431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago Chesterton 9.4/10 Exceptional (3) "I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) T J. CA $155 CA $553 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Fenced-Yard-Attached-Garagenear-Beach.h95038818.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bf2ce6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/57fac6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/87b39ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/9e1d8281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat w/Hot tub Indiana dunes Beaches Trails Chesterton 10/10 Exceptional (12) "This rental was amazing!!! So very clean, amazingly comfortable bed, and every amenity thought off. You will not be sorry that you stayed here. We hope to stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leiann N. CA $162 CA $379 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Chesterton-Hotels-Moody-Modern-Dunes-Hot-Tub-Beaches-Trails.h119048616.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23363/9161abd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/23400/23363/3e9029f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/30000/23400/23363/d5b77440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/1000000/30000/23400/23363/61993103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairbridge Inn Express Chesterton Chesterton 6.8/10 (343) "Staff were lovely " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jessica [](https://www.expedia.ca/Chesterton-Hotels-Fairbridge-Inn-Express-Chesterton.h23363.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w1024h569x0y58-4410e30f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w506h639x259y44-a4620252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/94fa6fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w533h639x246y44-3068c943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Beautiful Riverfront Home on 10 Acres! Chesterton 8.0/10 Very good (9) "Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff S. CA $220 CA $541 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/NEW-Beautiful-Riverfront-Home-On-10-Acres.h74510787.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/fd0a141c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/2be992b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/e6eb7e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/742180b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Near Interstate I94 New Buffalo 8.4/10 Very good (1047) "Friendly staff - clean room!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $93 CA $99 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.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=2025-12-23&endDate=2025-12-24®ionId=7214&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## 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 "Room was wonderful, spacious, clean and convenient." [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.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 "Everything was great food and staff." [](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.Hotel-Information) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "Beautiful Hotel" [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.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 "nothing to say about it. was very lovely " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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 "Even though the gym was small, it was well equipped. The room was clean, no odd smells or marks anywhere, the beds were comfortable, well worth the cost" [](https://expedia.ca/Hammond-Hotels-Fairfield-Inn-Suites-By-Marriott-Chicago-SoutheastHammond.h62954.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 "Very kind staff, clean room and good breakfast service " [](https://expedia.ca/Merrillville-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Merrillville.h5258.Hotel-Information) ![Baymont by Wyndham Michigan City](https://images.trvl-media.com/lodging/1000000/30000/21300/21232/6321c49b_y.jpg) ### Baymont by Wyndham Michigan City 10/10 Excellent "Genament up front was very acomedeating " [](https://expedia.ca/Michigan-City-Hotels-Baymont-By-Wyndham-Michigan-City.h21232.Hotel-Information) ![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "Beautiful room " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.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 "Great staff and hospitality! Everything was clean and tidy. " [](https://expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ## Frequently asked questions ### What's Chesterton like for family-friendly vacations? ### What's the best place to stay for a family vacation in Chesterton? ### How many hotels that welcome families can I expect to find in Chesterton? ### When's the best time to book a family-friendly vacation in Chesterton? ### What's there to see and do with your family in Chesterton? ## 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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