Title: Chesterton Vacation Home Rentals from CA $219: Search Top Private Vacation Homes for Rent | 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) # Chesterton Vacation Rentals ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chesterton Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/5d50cb22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h955x0y0-2001df05.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) "The house was very clean and served us well. It was in a great walkable small town with plenty of good restaurants, and only a short drive to the dunes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue CA $100 CA $439 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chesterton-Hotels-Relaxing-3-Bedroom-I-2-Baths-I-2-Living-Rooms-Home.h89011067.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/a5e3e3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/3ab5736e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/ecb842fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/845afee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago Chesterton 8.6/10 Excellent (7) "Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick R. CA $119 CA $415 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Separate-Fenced-Yard-Beach.h95044250.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104450000/104442100/104442031/847f8f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104450000/104442100/104442031/481c9103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/105000000/104450000/104442100/104442031/8157684d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104450000/104442100/104442031/716b8c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes Chesterton 9.2/10 Wonderful (18) "This is a beautiful place. It has everything that you could possibly need. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George N. CA $188 CA $684 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chesterton-Hotels-Roomy-Retreat-Family-Friends2-King-BGame-Room-Valpo-University-Dunes.h104442031.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) ![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) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w906h683x59y0-555b2e8e.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 $222 CA $545 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/NEW-Beautiful-Riverfront-Home-On-10-Acres.h74510787.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/10848660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/7c357ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/5f3dcfa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat w/Hot tub Indiana dunes Beaches Trails Chesterton 10/10 Exceptional (10) "This was one of the nicest, cleanest VRBO we have stated in. Don’t let the neighborhood detour you from staying. We felt safe and slept amazing in the VERY comfy king bed !! The master shower drain wasn’t working during our stay but the owner was very responsive and apologized for the inconvenience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dot Dot Smile Nichole W. CA $276 CA $526 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chesterton-Hotels-Moody-Modern-Dunes-Hot-Tub-Beaches-Trails.h119048616.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/w1290h945x0y1-6626c3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113300000/113290100/113290024/c973d5b8.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) ![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) ### 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason B. 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) ![Beach nearby](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/4d6f849b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/9e42e19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/2d7c91c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/ac4e0b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago Michigan City 9.8/10 Exceptional (13) "It was very cozy and perfect! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tommy W. CA $119 CA $219 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Michigan-City-Hotels-New-Cozy-House-5-Min-To-Beach-Zoo-Restaurants-Casino-Brewery-Train-To-Chicago.h102853153.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/1904ee1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/f0ffd6b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/6e8eefad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/w1440h959x0y1-0c1e3d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Singing Sands Trl | Hot Tub Retreat | Dogs OK Michigan City 9.8/10 Exceptional (22) "We stayed for four nights with four children - the house was clean, well stocked with essentials for cooking and cleaning, and the kids loved the smore station and playing in the back yard. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill B. CA $138 CA $333 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Michigan-City-Hotels-SingingSands-Trl-Hottub-Retreat.h101944488.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104350000/104347800/104347785/0b0a10ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104350000/104347800/104347785/df57d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/105000000/104350000/104347800/104347785/b4f2d0d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104350000/104347800/104347785/0fe921ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown New Buffalo 9.6/10 Exceptional (5) "We really loved this house! Comfy beds, fun amenities (the converted garage hangout space is fabulous), great design/layout with plenty of room for everyone to spread out or all be together. The backyard was great, too! The location felt secluded, but everything is only a few minutes drive away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeana H. CA $124 CA $658 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/New-Buffalo-Hotels-Secluded-Oasis-4-Bedrooms.h104347785.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105100000/105098800/105098759/w2100h1399x0y1-98d8f1b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/106000000/105100000/105098800/105098759/w2099h1399x1y1-0c5db91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105100000/105098800/105098759/fa11119c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105100000/105098800/105098759/w2100h1399x0y1-af61c692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Boutique at Midtown Central / Hot Tub / Pet Friendly Michigan City 9.6/10 Exceptional (10) "We loved staying here. Jason was a great communicator and made sure our needs were met. Plenty of beds for our family of 8 adults. 10 minutes to the national park and its pristine beaches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy W. CA $165 CA $410 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Michigan-City-Hotels-The-Train-House-Michigan-City.h105098759.Hotel-Information) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/57e5f713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/a3448b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/e5af2c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/93e50e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach Michigan City 9.4/10 Exceptional (30) "House was very nice. Host was very responsive and kind." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa R. CA $112 CA $500 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Michigan-City-Hotels-Sand-Sun-Retreat.h100107758.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105820000/105813500/105813403/c4493385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105820000/105813500/105813403/f78f9a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105820000/105813500/105813403/693bdc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105820000/105813500/105813403/db535a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Bliss: Steps to Beach + Hot Tub Michigan City 9.6/10 Exceptional (16) "All went perfectly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David A. CA $139 CA $637 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Michigan-City-Hotels-Beachside-Bliss-Steps-To-Beach.h105813403.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102610000/102604000/102603902/w905h683x59y0-75adbc0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/103000000/102610000/102604000/102603902/w904h683x60y0-e92b2fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102610000/102604000/102603902/9c456aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102610000/102604000/102603902/w903h683x60y0-224c1db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dunes Cottage at Town of Pines Lake Michigan near Indiana Dunes Parks! Town of Pines 9.8/10 Exceptional (15) "I loved this house, reminded me of grandma, hosts had things labeled and organized. Simple easy to follow instructions. Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorraine L. CA $119 CA $419 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Town-Of-Pines-Hotels-Dunes-Cottage-At-Town-Of-Pines-Lake-Michigan-Near-Indiana-Dunes-Parks.h102603902.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/428b4b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/20ddc9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/f7f8c3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/26d5ff9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duplex | Firepit | Game Room | Hot Tub-all year Michigan City 8.6/10 Excellent (17) "Home very well stocked, very cute and clean inside. We're able to walk to restaurants and Sheridan beaches. Very friendly and safe area. Wine tasting, golfing and excellent restaurants nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marie H. CA $98 CA $283 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Michigan-City-Hotels-Family-Beach-Fun-Spot-Firepit-Games-FireTV.h82495809.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/5bde82d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/830542f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/e9ccc0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/3c9679cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-bedroom house in charming La Porte three minute walk to beautiful Stone Lake La Porte 9.8/10 Exceptional (6) "Nice layout of the home for our group. Good location. We had a very nice time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa C. CA $264 CA $439 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/La-Porte-Hotels-3-Bedroom-House-In-Charming-La-Porte-Three-Minute-Walk-To-Beautiful-Stone-Lake.h113298890.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91120000/91117100/91117026/6db6894d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91120000/91117100/91117026/aaa47651.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91120000/91117100/91117026/9ccacd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books, stereo](https://images.trvl-media.com/lodging/92000000/91120000/91117100/91117026/ac748a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bed 3 Ba Screenporch/Sunset Lake Views LaPorte, Indiana, US 10/10 Exceptional (66) "Possibly the perfect place for an adult family weekend. House was nicer and even better appointed than expected. Owners have anticipated and exceeded guest needs for comfort and enjoyment. Would absolutely stay again if visiting the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer G. CA $300 CA $756 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/La-Porte-Hotels-CaLLinG-All-LaKe-LoVers.h91117026.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/105000000/104140000/104130800/104130724/b5a85fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104140000/104130800/104130724/b4bb6d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104140000/104130800/104130724/5f7badc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104140000/104130800/104130724/70b90a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy home near Lake Michigan with Smart TVs, fast Wi-Fi, and rustic charm. Michigan City 9.8/10 Exceptional (7) "Very comfortable and beautiful property equipped with everything you need. Location is fabulous and communication was everything we could have wanted and more. Will definitely be my go to stay when visiting the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derhonda T. CA $201 CA $386 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Michigan-City-Hotels-Cozy-Home-Near-Lake-Michigan-With-Smart-TVs.h104130724.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/108000000/107230000/107226700/107226653/07929948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/108000000/107230000/107226700/107226653/74d655a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107230000/107226700/107226653/2443eac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107230000/107226700/107226653/92de4bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilltop Cove- Charming 2 bed/2 bath in Beachwalk Resort with Golf Cart! Michigan City 9.8/10 Exceptional (16) "Our family thoroughly enjoyed our stay at Hilltop Cove! We will definitely visit again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $282 CA $766 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Michigan-City-Hotels-Hilltop-Cove-Charming-2-Bed-2-Bath-In-Beachwalk-Resort-With-Golf-Cart.h107226653.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/83000000/82510000/82504100/82504096/4abf8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82510000/82504100/82504096/4b177a83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/83000000/82510000/82504100/82504096/2171d52b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82510000/82504100/82504096/a2cf33fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK Michigan City 9.6/10 Exceptional (47) "Liked the location, hot tub was great.Walked to the zoo." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian M. CA $138 CA $460 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Michigan-City-Hotels-Close-To-Beach-Hot-Tub-Game-Rm-Firepit.h82504096.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/82000000/81170000/81166100/81166060/5aeb569d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/82000000/81170000/81166100/81166060/2ec8f483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/82000000/81170000/81166100/81166060/37421f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81170000/81166100/81166060/49076b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Zen | HotTub-all yr | Firepit | Grill | DogsOK Michigan City 9.6/10 Exceptional (34) "We had an amazing time! Enjoyed every part of the house " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Florence U. CA $152 CA $350 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Michigan-City-Hotels-Beach-Retreat-Hot-Tub-Firepit-Grill.h81166060.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=2025-11-13&endDate=2025-11-14®ionId=7214&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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-Private-Vacation-Homes.d7214-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterton-Private-Vacation-Homes.d7214-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chesterton Hotel Reviews ![Tru By Hilton Merrillville](//images.trvl-media.com/lodging/101000000/100810000/100803500/100803423/f4f30336_y.jpg) ### Tru By Hilton Merrillville 10/10 Excellent "Room was clean, staff was friendly" [](https://expedia.ca/Merrillville-Hotels-Tru-By-Hilton-Merrillville.h100803423.Hotel-Information) ![Four Winds Casino Resort – New Buffalo](//images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139_y.jpg) ### Four Winds Casino Resort – New Buffalo 10/10 Excellent "Efficient check in. Very good value. Great public areas and spacious comfortable room. Entrance for hotel not clearly marked (cf.casino entrance). Friendly and cordial staff in hotel. We did not visit either the casino or restaurant areas. Nice amenities in hotel. Would stay here again. Location is at edge of New Buffalo in area with woods and deer." [](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Waterbird Lakeside Inn](//images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "Loved the balcony overlooking the lake " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Motel 6 Merrillville, IN](//images.trvl-media.com/lodging/1000000/60000/50500/50475/2c229b01_y.jpg) ### Motel 6 Merrillville, IN 10/10 Excellent "It was great, best little getaway 😊" [](https://expedia.ca/Merrillville-Hotels-Motel-6-Merrillville.h50475.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 "Michigan City leaves a little to be desired, but the Blue Chip is a nice property with good food and reasonable room rates. I would come here again." [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![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 "All good. Would go back." [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.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 "The breakfast was very healthy oriented.The view from the hotel was beautiful. Plenty of parking, but it's located behind other things.So it was not kept up very well. The staff was very friendly and helpful.When we asked for suggestions on where to have dinner" [](https://expedia.ca/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.Hotel-Information) ![Spring House Inn](//images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "Very nice and clean unique Inn. Very cool location." [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Ameristar Casino Hotel East Chicago](//images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg) ### Ameristar Casino Hotel East Chicago 10/10 Excellent "Dave from front desk was amazing, extremely friendly and helpful. Room was great, clean, and comfortable bed. Staff we encountered were all so friendly and welcoming. Definitely will stay here again!!" [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ## Find out more about Chesterton ## Chesterton Vacation Homes information | Number of reviews | 398 | | --- | --- | | Accommodation | 740 Vacation Homes | | Lowest Price | CA $219 | | Highest Price | CA $812 | ## 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) - 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