Book Holiday Homes in Chesterton
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Chesterton

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

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Journey To Valpo | Home Near Downtown!

Miller Beach Blue Door By The Shore #2

"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly

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

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

Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!
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 | 635 Holiday Homes |
---|---|
Lowest Price | AU$151 |
Highest Price | AU$180 |
Popular accommodation | Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna, Journey To Valpo | Home Near Downtown!, Miller Beach Blue Door By The Shore #2 , "The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room, Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly, Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub, Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town, Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!! |
Holiday Homes in Chesterton
Top Locations for Holiday Homes in Chesterton
More accommodations in Chesterton
Top trending hotels in Chesterton

Spring House Inn

Best Western Indian Oak

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

Hilton Garden Inn Chesterton
More ways to explore Chesterton
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.