Book Holiday Homes in Chesterton
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Featured Holiday Homes in Chesterton

Miller Beach Blue Door By The Shore #2

Sweet Stay By-The-Lake in Michigan City with AC, WiFi

Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town

Roomy and Cozy 3bd 2ba just mins from Indiana Dunes

Walk to the beach! Great modern home with spring and early summer availability!
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 | 757 Holiday Homes |
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Lowest Price | AU$151 |
Highest Price | AU$545 |
Popular accommodation | Miller Beach Blue Door By The Shore #2 , Sweet Stay By-The-Lake in Michigan City with AC, WiFi, Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub, Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13, Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St, Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town, Roomy and Cozy 3bd 2ba just mins from Indiana Dunes, Walk to the beach! Great modern home with spring and early summer availability! |
Holiday Homes in Chesterton
Top Locations for Holiday Homes in Chesterton
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Spring House Inn

Best Western Indian Oak

Hilton Garden Inn Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
More ways to explore Chesterton
Top picks
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^Subject to availability and chosen travel dates.