Book Holiday Homes in Chesterton

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Featured Holiday Homes in Chesterton

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

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

Michigan City
When you stay at this vacation home in Michigan City, you'll be near the beach, within a 5-minute drive of Lake Michigan and Blue Chip Casino.
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

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

Michigan City
With a stay at this vacation home in Michigan City, you'll be a 2-minute drive from Lake Michigan and 8 minutes from Blue Chip Casino.
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Journey To Valpo | Home Near Downtown!

Journey To Valpo | Home Near Downtown!

Valparaiso
With a stay at this vacation home in Valparaiso, you'll be within a 5-minute drive of Chicago Street Theatre and Memorial Opera House.
Journey To Valpo | Home Near Downtown!
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Miller Beach Blue Door By The Shore #2

Miller Beach Blue Door By The Shore #2

Gary
Located in Gary (Miller Beach), this vacation home is steps from Lake Michigan and a 2-minute drive from Indiana Dunes National Park.
Miller Beach Blue Door By The Shore #2
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

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

Porter
With a stay at this vacation home, you'll be centrally located in Chesterton, within a 5-minute drive of Indiana Dunes National Park and Indiana Dunes State ...
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly

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

2 out of 5
New Buffalo
Located in New Buffalo, this vacation home is within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.
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 Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

New Buffalo
When you stay at this vacation home in New Buffalo, you'll be on a lake, within a 15-minute drive of Lake Michigan and Blue Chip Casino.
Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub
 Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town

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

New Buffalo
With a stay at this vacation home in New Buffalo, you'll be within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.
Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town
Modern Farmhouse - steps from downtown!!  Stay 2-nights, get 1 free thru March!!

Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!

New Buffalo
With a stay at this vacation home, you'll be centrally located in New Buffalo, a 3-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New ...
Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!
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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.

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!!

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
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.