Book Holiday Homes in Chesterton

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Featured Holiday Homes in Chesterton

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Michigan City IN
Stay at this holiday home in Michigan City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Blue Chip Casino and Barker Mansion are located ...
Opens in a new windowRed Zen | HotTub-all yr | Firepit | Grill | DogsOK
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Gary IN
The price is NZ$776 per night from 23 Dec to 24 Dec
NZ$776
23 Dec - 24 Dec
includes taxes & fees
Stay at this family-friendly holiday home in Gary. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Gary SouthShore RailCats ...
Opens in a new window15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
New Private Pool Opening May 2023,  Hot Tub, Renovated Home, Ping Pong Table!

New Private Pool Opening May 2023, Hot Tub, Renovated Home, Ping Pong Table!

New Buffalo MI
Stay at this family-friendly holiday home in New Buffalo. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Four Winds Casino New Buffalo ...
Opens in a new windowNew Private Pool Opening May 2023, Hot Tub, Renovated Home, Ping Pong Table!
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Hot tub & Pool in Gorgeous Wooded Community

Hot tub & Pool in Gorgeous Wooded Community

New Buffalo MI
Stay at this family-friendly holiday home in New Buffalo. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Four Winds Casino New Buffalo and ...
Opens in a new windowHot tub & Pool in Gorgeous Wooded Community
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

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

Michigan City IN
Stay at this holiday home in Michigan City. Enjoy free Wi-Fi, laundry facilities and tennis courts. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowBeautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
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 IN
Stay at this family-friendly holiday home in Michigan City. Enjoy laundry facilities, tennis courts and a pool table. Popular attractions Blue Chip Casino and ...
Opens in a new windowFamily Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
The Cypress Log Cabin - Historic National Park Home on the beach

The Cypress Log Cabin - Historic National Park Home on the beach

2 out of 5
Michigan City IN
Stay at this beach holiday home in Michigan City. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Indiana Dunes National Park and ...
Opens in a new windowThe Cypress Log Cabin - Historic National Park Home on the beach
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Michigan City IN
The price is NZ$691 per night from 28 Dec to 29 Dec
NZ$691
28 Dec - 29 Dec
includes taxes & fees
Stay at this family-friendly holiday home in Michigan City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Blue Chip Casino and Winding ...
Opens in a new windowSand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart.  Great family house

Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Michigan City IN
Stay at this family-friendly holiday home in Michigan City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Blue Chip Casino and Sand ...
Opens in a new windowBeachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house
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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
723 Holiday Homes
Lowest Price
NZ$162
Highest Price
NZ$776
Popular accommodation
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK, 15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly, New Private Pool Opening May 2023, Hot Tub, Renovated Home, Ping Pong Table!, Hot tub & Pool in Gorgeous Wooded Community, Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven., Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, The Cypress Log Cabin - Historic National Park Home on the beach, Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach, Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Top trending hotels in Chesterton

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 out of 5
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 28 Dec to 29 Dec
NZ$175
28 Dec - 29 Dec
includes taxes & fees
Stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowComfort Inn & Suites Porter near Indiana Dunes
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 NZ$162 per night from 1 Jan to 2 Jan
NZ$162
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowSpring 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 NZ$206 per night from 30 Dec to 31 Dec
NZ$206
30 Dec - 31 Dec
includes taxes & fees
Stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff ...
Opens in a new windowHilton Garden Inn Chesterton
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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 NZ$182 per night from 28 Dec to 29 Dec
NZ$182
28 Dec - 29 Dec
includes taxes & fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowBest Western Indian Oak
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.

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^Subject to availability and chosen travel dates.