Book Holiday Homes in Chesterton

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Chesterton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesterton vacation homes are the perfect way for you to wing it.

Holiday houses in Chesterton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesterton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesterton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesterton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesterton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesterton Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$151
Highest Price
AU$562
Popular accommodation
Spring House Inn, Best Western Indian Oak, Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly, Hilton Garden Inn Chesterton

Top trending hotels in Chesterton

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 16 Mar to 17 Mar
AU$158
includes taxes & fees
16 Mar - 17 Mar
When you stay at Spring House Inn in Chesterton, you'll be in a national park, within a 5-minute drive of Indiana Dunes National Park and Indiana Dunes State ...
Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 9 Apr to 10 Apr
AU$151
includes taxes & fees
9 Apr - 10 Apr
When you stay at Best Western Indian Oak in Chesterton, you'll be on the waterfront, within a 5-minute drive of Indiana Dunes National Park and Indiana Dunes ...
Best Western Indian Oak
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Porter
The price is AU$562 per night from 21 Mar to 22 Mar
AU$562
includes taxes & fees
21 Mar - 22 Mar
Located in Chesterton (Porter Beach), this cabin is steps from Lake Michigan and a 2-minute drive from Indiana Dunes State Park.
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
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Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 30 Mar to 31 Mar
AU$180
includes taxes & fees
30 Mar - 31 Mar
When you stay at Hilton Garden Inn Chesterton in Chesterton, you'll be in the business district, within a 10-minute drive of Indiana Dunes National Park and ...
Hilton Garden Inn Chesterton
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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.

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^Subject to availability and chosen travel dates.