Title: Book the Best Hotels with POOL in Chesterton in 2025 | 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) ![Indiana Dunes State Park showing general coastal views and a beach as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/232000/232034-Indiana-Dunes-State-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Chesterton, IN from CA $146 ![](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 Hotels with a Pool Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-10&endDate=2025-10-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesterton Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/2c46627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/76227ea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/14950785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/cdd66cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spring House Inn Chesterton 9.0/10 Wonderful (1013) "We enjoy our stay. " CA $138 CA $162 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/aac1dd4d.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/858300/858225/87c7ddbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chesterton Chesterton 8.8/10 Excellent (1003) "Awesome! Try Fluid Coffee! " CA $161 CA $181 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chesterton-Hotels-Hilton-Garden-Inn-Chesterton.h858225.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/980de117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/77291ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/527d397d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/ddafc438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Indian Oak Chesterton 8.6/10 Excellent (1007) "Nice hotel with easy access to the lakefront" CA $130 CA $146 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb.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 (1008) "Nice and close to the beach." CA $152 CA $170 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/w894h683x65y0-0fccdb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/16d6c865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/8828ea53_edited_df58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/47cadd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The "Pool Barn Camper" w/Hot Tub near Indiana Dunes Porter 8.8/10 Excellent (11) "Great pool hostess was very helpful" CA $162 CA $213 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chesterton-Hotels-The-Pool-Barn-Camper-WHot-Tub-Near-Indiana-Dunes.h69385955.Hotel-Information) ![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/70000000/69390000/69385700/69385681/10372699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/94b9ad4a.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 property. Close to the dunes and an amazing amount of hospitality from the owners, who are local enough to assist with any issues. Definitely would stay again!" CA $207 CA $263 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chesterton-Hotels-The-Pool-Barn-WPool.h69385681.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/c973d5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/12610d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/w1290h945x0y1-6626c3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/71354484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### After-Dune Delight! Large Home with Pool and Fun for All Porter 10/10 Exceptional (1) "The property was clean and well maintained. The host was responsive and nice. We had a wonderful stay here." CA $353 CA $812 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chesterton-Hotels-After-Dune-Delight-A-Perfect-Getaway.h113290024.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/9826a884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/34b60a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/a7566650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/70c2b529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Winds Casino Resort – New Buffalo New Buffalo 9.4/10 Exceptional (1544) "Such a great time the hotel was wonderful " CA $137 CA $159 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/1c27010a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/2a51d1b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/a255c4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/394b8177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites New Buffalo by IHG New Buffalo 8.8/10 Excellent (1004) "Amazing service; my favorite place to stay when I come to New Buffalo! " CA $151 CA $160 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Benton-Harbor-Hotels-Holiday-Inn-Express-Suites-New-Buffalo.h543985.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/220000/212400/212371/38ae14dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/220000/212400/212371/52c70fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/220000/212400/212371/81298119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/220000/212400/212371/f8a8b186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Portage Portage 7.8/10 Good (793) "Safe, friendly staffs, right by expressway, plenty of parking, breakfast is ok, room is ok" CA $136 CA $152 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Portage-Hotels-Hampton-Inn-Portage.h212371.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=2025-10-23&endDate=2025-10-24®ionId=7214&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![Quality Inn Near Interstate I94](//images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg) ### Quality Inn Near Interstate I94 10/10 Excellent "They had a great breakfast bar" [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Spring House Inn](//images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "good hotel" [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Fairfield Inn and Suites By Marriott Merrillville](//images.trvl-media.com/lodging/1000000/10000/5300/5258/b28d063e_y.jpg) ### Fairfield Inn and Suites By Marriott Merrillville 10/10 Excellent "Breakfast was wonderful with the staff there very polite and helpful!" [](https://expedia.ca/Merrillville-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Merrillville.h5258.Hotel-Information) ![Best Western Indian Oak](//images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg) ### Best Western Indian Oak 10/10 Excellent "Ac was great, room was spacious and comfortable, patio view was very nice, National and State Park near by, great restaurant selections and some within walking distance. Rooms were clean, plenty of parking, and a very quiet area." [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![Blue Chip Casino Hotel and Spa](//images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg) ### Blue Chip Casino Hotel and Spa 10/10 Excellent "Wanted Lake view but they said NO" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Baymont by Wyndham Michigan City](//images.trvl-media.com/lodging/1000000/30000/21300/21232/6321c49b_y.jpg) ### Baymont by Wyndham Michigan City 10/10 Excellent "Parking was easy with cameras. Staff helped recover my gf lost phone. Very happy with our service and stay! Breakfast was better than most places. " [](https://expedia.ca/Michigan-City-Hotels-Baymont-By-Wyndham-Michigan-City.h21232.Hotel-Information) ![Comfort Inn & Suites Porter near Indiana Dunes](//images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb_y.jpg) ### Comfort Inn & Suites Porter near Indiana Dunes 10/10 Excellent "Nice and close to the beach." [](https://expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ![Baymont by Wyndham New Buffalo](//images.trvl-media.com/lodging/1000000/870000/867300/867230/6dac1343_y.jpg) ### Baymont by Wyndham New Buffalo 10/10 Excellent "Stay for business every week!" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Waterbird Lakeside Inn](//images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "Nice, big rooms with a beautiful view of the lake. The room was clean and comfortable. Would recommend for the price." [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chesterton? > [Waterbird Lakeside Inn](https://www.expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information): Hotel, 10-minute walk from Indiana Dunes National Park. Offers a sauna, an indoor pool, and daily. [Spring House Inn](https://www.expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information): Hotel located near Indiana Dunes National Park. Provides a sauna, an indoor pool, and free self parking. [Best Western Indian Oak](https://www.expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information): Hotel located near Indiana Dunes National Park. Features daily, an indoor pool, and free self parking. [Comfort Inn & Suites Porter near Indiana Dunes](https://www.expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information): Offers a snack bar/deli, an indoor pool, and free self parking. [Hilton Garden Inn Chesterton](https://www.expedia.ca/Chesterton-Hotels-Hilton-Garden-Inn-Chesterton.h858225.Hotel-Information): Hotel steps from Blue Chip Casino. Features 3 restaurants, an indoor pool, and a full-service spa. ### What is there to see and do in Chesterton? > Explore places like Indiana Dunes National Park and Lake Michigan while you're in Chesterton. Surround yourself with nature at Indiana Dunes Visitor Center and Coffee Creek Watershed Conservancy Preserve. The beaches, lakeside setting, and restaurants are just some of the things to enjoy while you're in the area. ### When is the best time to book a hotel with a pool in Chesterton? > You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Chesterton in the hottest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 31°F. ## 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) - [Cheap Hotels in Beverly Shores](https://www.expedia.ca/Beverly-Shores-Hotels-Cheap-Hotels.0-0-d3000435761-tCheapHotels.Travel-Guide-Filter-Hotels) - [Beverly Shores Hotels](https://www.expedia.ca/Beverly-Shores-Hotels.d3000435761.Travel-Guide-Hotels) - [Burns Harbor Hotels](https://www.expedia.ca/Burns-Harbor-Hotels.d553248634983526861.Travel-Guide-Hotels) - 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