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
The price is NZ$426 per night from 16 Feb to 17 Feb
NZ$426
16 Feb - 17 Feb
includes taxes & fees
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
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
The price is NZ$817 per night from 20 Feb to 21 Feb
NZ$817
20 Feb - 21 Feb
includes taxes & fees
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$654 per night from 22 Feb to 23 Feb
NZ$654
22 Feb - 23 Feb
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 Cleveland ...
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$149
Highest Price
NZ$817
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$149 per night from 18 Feb to 19 Feb
NZ$149
18 Feb - 19 Feb
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$155 per night from 16 Feb to 17 Feb
NZ$155
16 Feb - 17 Feb
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
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
Stay at this hotel in Chesterton. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowWaterbird Lakeside Inn
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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 NZ$190 per night from 1 Mar to 2 Mar
NZ$190
1 Mar - 2 Mar
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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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.