Book Holiday Homes in Chesterton

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Featured Holiday Homes in Chesterton

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

New Buffalo
Book a stay at this family-friendly vacation home in New Buffalo. Enjoy free WiFi, private pools, and patios. Our guests praise the pool in our reviews. Popular ...
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City
Book a stay at this family-friendly vacation home in Michigan City. Enjoy a garden, patios, and cable/satellite TV service. Our guests praise the bathrooms in ...
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches

Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches

Michigan City
Book a stay at this family-friendly vacation home in Michigan City. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Four Winds Casino New Buffalo ...
Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches
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cozy home with hot tub next to downtown Valparaiso

cozy home with hot tub next to downtown Valparaiso

Valparaiso
Book a stay at this family-friendly vacation home in Valparaiso. Enjoy free WiFi, a water park, and a garden. Popular attractions Chicago Street Theatre and ...
cozy home with hot tub next to downtown Valparaiso
Nestled just behind Marquette Park. 5 minute walk to beach.

Nestled just behind Marquette Park. 5 minute walk to beach.

Gary
Stay at this vacation home in Gary. Enjoy free WiFi, a garden, and patios. Popular attractions Marquette Park and Marquette Beach are located nearby.
Nestled just behind Marquette Park. 5 minute walk to beach.
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes

Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes

Chesterton
The price is NZ$937 per night from 30 Dec to 31 Dec
NZ$937
includes taxes & fees
30 Dec - 31 Dec
Book a stay at this family-friendly vacation home in Chesterton. Enjoy free WiFi, a garden, and patios. Popular attractions Indiana Dunes National Park and Lustron ...
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

Michigan City
The price is NZ$736 per night from 2 Jan to 3 Jan
NZ$736
includes taxes & fees
2 Jan - 3 Jan 2025
Book a stay at this family-friendly vacation home in Michigan City. Enjoy free WiFi, a water park, and a garden. Popular attractions Cleveland Park and Winding ...
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!

Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!

Michigan City
Book a stay at this family-friendly vacation home in Michigan City. Enjoy free WiFi, a water park, and a garden. Popular attractions Putting Green Park and Central ...
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Miller Beach
Book a stay at this beach vacation home in Gary. Enjoy free WiFi, a sauna, and a garden. Popular attractions Lake Street Beach and Marquette Park are located ...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
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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
611 Holiday Homes
Lowest Price
NZ$168
Highest Price
NZ$937
Popular accommodation
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!, Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!, Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches , cozy home with hot tub next to downtown Valparaiso, Nestled just behind Marquette Park. 5 minute walk to beach., Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes, Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly, Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!, Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

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 NZ$176 per night from 24 Dec to 25 Dec
NZ$176
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 NZ$168 per night from 29 Dec to 30 Dec
NZ$168
includes taxes & fees
29 Dec - 30 Dec
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. ...
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
The price is NZ$519 per night from 6 Jan to 7 Jan
NZ$519
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this cabin in Chesterton. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular attractions ...
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 NZ$214 per night from 1 Jan to 2 Jan
NZ$214
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff 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.