Title: Chesterton Vacation Rentals from $88: Search Short-Term Rentals | Expedia.com

[Chesterton Travel Guide](https://expedia.com/Chesterton.dx7214)[Hotels in Chesterton](https://expedia.com/Chesterton-Hotels.d7214.Travel-Guide-Hotels)[Flights to Chesterton](https://expedia.com/Cheap-Flights-To-Chesterton.d7214.Travel-Guide-Flights)[Things to do in Chesterton](https://expedia.com/Things-To-Do-In-Chesterton.d7214.Travel-Guide-Activities)[Car Rentals in Chesterton](https://expedia.com/Car-Rentals-In-Chesterton.d7214.Car-Rental-Guide)[Chesterton Vacation Packages](https://expedia.com/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)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL)

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## 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

"."

[](https://expedia.com/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information)

![Quality Inn Near Interstate I94](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg)

### Quality Inn Near Interstate I94

10/10 Excellent

"Clean room and comfy bed"

[](https://expedia.com/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.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

"Very courteous service, room was perfect! Hot coffee and breakfast in morning. Highly recommend 👌 "

[](https://expedia.com/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.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

"The room was great and Clean The bed was very Comfortable"

[](https://expedia.com/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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

"Yes room was perfect! "

[](https://expedia.com/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.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

"The staff was very accommodating, the room very clean and comfortable and the breakfast buffet was delicious! I will stay again."

[](https://expedia.com/Hammond-Hotels-Fairfield-Inn-Suites-By-Marriott-Chicago-SoutheastHammond.h62954.Hotel-Information)

![Comfort Inn Hobart-Merrillville I-65](https://images.trvl-media.com/lodging/1000000/50000/42500/42459/d222dd8e_y.jpg)

### Comfort Inn Hobart-Merrillville I-65

10/10 Excellent

"Room was clean and staff was friendly."

[](https://expedia.com/Hobart-Hotels-Comfort-Inn-Hobart-Merrillville.h42459.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

"Yes"

[](https://expedia.com/Hammond-Hotels-Motel-6-Hammond.h1037771.Hotel-Information)

![FairBridge Inn Express Merrillville](https://images.trvl-media.com/lodging/1000000/130000/123900/123860/39572dda_y.jpg)

### FairBridge Inn Express Merrillville

10/10 Excellent

"The room was one of the best rooms I had ever stayed in. Im glad the Redroof canceled my room brcause Fairbridge was way better spacy and had space for me and my family to sleep comfortable. Staff was also great!!!"

[](https://expedia.com/Merrillville-Hotels-FairBridge-Inn-Express-Merrillville.h123860.Hotel-Information)

## Find out more about Chesterton

**Everything you need to know about Chesterton vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chesterton vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesterton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chesterton rentals**

At Expedia, we put the best Chesterton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [Vacation Homes in Chesterton ](https://expedia.com/Chesterton-Private-Vacation-Homes.d7214-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chesterton ](https://expedia.com/Chesterton-Apartments.d7214-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chesterton ](https://expedia.com/Chesterton-Cottages.d7214-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Chesterton ](https://expedia.com/Chesterton-Condos.d7214-aaCondos.Travel-Guide-Accommodation)
- [Guest Houses in Chesterton ](https://expedia.com/Chesterton-Guest-Houses.d7214-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Chesterton ](https://expedia.com/Chesterton-Motels.d7214-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesterton ](https://expedia.com/Chesterton-Cabins.d7214-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Chesterton ](https://expedia.com/Chesterton-Agritourism.d7214-aaAgritourism.Travel-Guide-Accommodation)
- [RV Parks in Chesterton ](https://expedia.com/Chesterton-RV-Parks.d7214-aaRVParks.Travel-Guide-Accommodation)
- [Villas in Chesterton ](https://expedia.com/Chesterton-Villas.d7214-aaVillas.Travel-Guide-Accommodation)
- [Aparthotels in Chesterton ](https://expedia.com/Chesterton-Apart-Hotels.d7214-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chesterton ](https://expedia.com/Chesterton-Inns.d7214-aaInns.Travel-Guide-Accommodation)
- [B&B in Chesterton ](https://expedia.com/Chesterton-Bed-And-Breakfast.d7214-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chesterton?

### What's the top vacation rental that Chesterton has to offer?

### How many vacation rentals are there in Chesterton?

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### What are vacation rentals like in Chesterton?

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