Book Holiday Homes in Chesterton

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Featured Holiday Homes in Chesterton

3br Home Minutes from Indiana Dunes State Park & Blue Chip Casino!

3br Home Minutes from Indiana Dunes State Park & Blue Chip Casino!

Michigan City
The price is AU$427 per night from 7 Jun to 8 Jun
AU$427
per night
7 Jun - 8 Jun
With a stay at this vacation home in Michigan City, you'll be within a 5-minute drive of Lake Michigan and Blue Chip Casino.
3br Home Minutes from Indiana Dunes State Park & Blue Chip Casino!
Dunes Escape - Minutes from Indiana Dunes National Park

Dunes Escape - Minutes from Indiana Dunes National Park

Gary
The price is AU$492 per night from 27 Jun to 28 Jun
AU$492
per night
27 Jun - 28 Jun
With a stay at this vacation home in Gary (Miller Beach), you'll be a 1-minute drive from Indiana Dunes National Park and 6 minutes from Lake Michigan.
Dunes Escape - Minutes from Indiana Dunes National Park
Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!

Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!

MICHIGAN CITY
The price is AU$910 per night from 9 Jun to 10 Jun
AU$910
per night
9 Jun - 10 Jun
With a stay at this vacation home in Michigan City, you'll be within a 5-minute drive of Lake Michigan and Blue Chip Casino.
Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!
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Just as the title says: Comfy Cozy.   Very cute house in a quiet residential neighborhood.

Just as the title says: Comfy Cozy. Very cute house in a quiet residential neighborhood.

Michigan City
The price is AU$464 per night from 5 Jun to 6 Jun
AU$464
per night
5 Jun - 6 Jun
With a stay at this vacation home in Michigan City, you'll be within a 5-minute drive of Indiana Dunes National Park and Blue Chip Casino.
Just as the title says: Comfy Cozy. Very cute house in a quiet residential neighborhood.
New Buffalo home w/prime Location Hot tub Gas Firepit Walk to All Fenced yard

New Buffalo home w/prime Location Hot tub Gas Firepit Walk to All Fenced yard

New Buffalo
When you stay at this vacation home in New Buffalo, you'll be near the beach, within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.
New Buffalo home w/prime Location Hot tub Gas Firepit Walk to All Fenced yard
The Whit-Just listed-pool, hot tub & more!

The Whit-Just listed-pool, hot tub & more!

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 10 minutes from Four Winds Casino New ...
The Whit-Just listed-pool, hot tub & more!
Castaway Villas- Pool, Hot Tub, near beach

Castaway Villas- Pool, Hot Tub, near beach

New Buffalo
With a stay at this vacation home, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New ...
Castaway Villas- Pool, Hot Tub, near beach
Beautiful Family Cottage in Beachwalk *Grill *AC * Free Wifi*Kids Haven.

Beautiful Family Cottage in Beachwalk *Grill *AC * Free Wifi*Kids Haven.

Michigan City
With a stay at this vacation home in Michigan City, you'll be within a 5-minute drive of Lake Michigan and Blue Chip Casino.
Beautiful Family Cottage in Beachwalk *Grill *AC * Free Wifi*Kids Haven.
Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

Michigan City
The price is AU$607 per night from 5 Jun to 6 Jun
AU$607
per night
5 Jun - 6 Jun
When you stay at this vacation home in Michigan City, you'll be on a lake, within a 5-minute drive of Lake Michigan and Blue Chip Casino.
Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach
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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
620 Holiday Homes
Lowest Price
AU$199
Highest Price
AU$910
Popular accommodation
3br Home Minutes from Indiana Dunes State Park & Blue Chip Casino!, Dunes Escape - Minutes from Indiana Dunes National Park, Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach! , Just as the title says: Comfy Cozy. Very cute house in a quiet residential neighborhood., New Buffalo home w/prime Location Hot tub Gas Firepit Walk to All Fenced yard, The Whit-Just listed-pool, hot tub & more!, Castaway Villas- Pool, Hot Tub, near beach, Beautiful Family Cottage in Beachwalk *Grill *AC * Free Wifi*Kids Haven., Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

Top trending hotels in Chesterton

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$201 per night from 5 Jun to 6 Jun
AU$201
per night
5 Jun - 6 Jun
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
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
The price is AU$199 per night from 5 Jun to 6 Jun
AU$199
per night
5 Jun - 6 Jun
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
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$213 per night from 16 Jun to 17 Jun
AU$213
per night
16 Jun - 17 Jun
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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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
Don't see what you're looking for?
See all available properties in 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.