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Chesterton vacation rentals

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Best Chesterton vacation rentals

Most recommended vacation rentals in Chesterton

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Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes - Chesterton - Beach
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton, IN
Free Wi-Fi
$111+
Check availability
Dunes Home 3 Bedroom I 2 Baths I 2 Living rooms - Chesterton - Living room
Dunes Home 3 Bedroom I 2 Baths I 2 Living rooms
Chesterton, IN
9.3Wonderful(47)
Parking
Free Wi-Fi
Pet friendly
$297+
Check availability
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago - Chesterton - Balcony
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Chesterton, IN
$135+
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Your Midwest Dunes Vacation Tri-State Paradise! - Chesterton - Kitchen
Your Midwest Dunes Vacation Tri-State Paradise!
Chesterton, IN
9.8Wonderful(53)
Parking
Free Wi-Fi
$295+
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Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes - Chesterton - Living room
Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes
Chesterton, IN
$399+
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Blue Birdhouse - Indiana Dunes - Pet Friendly - Chesterton - Patio
Blue Birdhouse - Indiana Dunes - Pet Friendly
Chesterton, IN
9.2Wonderful(26)
Parking
Free Wi-Fi
Pet friendly
$396+
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Bird`s Nest in the Indiana Dunes - Chesterton - Living room
Bird`s Nest in the Indiana Dunes
Chesterton, IN
$180+
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Private Kayak Launch and Zip Line Near the Dunes - Chesterton - Patio
Private Kayak Launch and Zip Line Near the Dunes
Chesterton, IN
Free Wi-Fi
$480+
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Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago - Chesterton - Bedroom
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton, IN
9.5Wonderful(9)
$148+
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Cozy Abode about 3 Mi to Indiana Dunes Natl Park - Chesterton - Living room
Cozy Abode about 3 Mi to Indiana Dunes Natl Park
Chesterton, IN
9.3Wonderful(10)
Free Wi-Fi
$1,186+
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National Park Nature Lover's Paradise w/ access to Chicago and Beach - Chesterton - Living room
National Park Nature Lover's Paradise w/ access to Chicago and Beach
Chesterton, IN
Free Wi-Fi
$315+
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Indiana Dunes/Lake Michigan/Downtown Chesterton - Chesterton - Living room
Indiana Dunes/Lake Michigan/Downtown Chesterton
Chesterton, IN
Free Wi-Fi
$395+
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Spacious 4 BR 10 mins to Near Chicago Sleeps 12 - Chesterton - Living room
Spacious 4 BR 10 mins to Near Chicago Sleeps 12
Chesterton, IN
Free Wi-Fi
$449+
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Roomy Retreat-Family & Friends 2 King Bed Game Room - Chesterton - Living room
Roomy Retreat-Family & Friends 2 King Bed Game Room
Chesterton, IN
10Wonderful(4)
Parking
Pet friendly
$535+
Check availability
Indiana Dunes Downtown 4 Bedroom House Dog Friendly 4 Miles to Beach - Chesterton
Indiana Dunes Downtown 4 Bedroom House Dog Friendly 4 Miles to Beach
Chesterton, IN
Free Wi-Fi
Pet friendly
$314+
Check availability
New! Quaint Chesterton Home In Walkable Location! - Chesterton
New! Quaint Chesterton Home In Walkable Location!
Chesterton, IN
$242+
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Good to know

Low season

November

High season

April

Average price (weeknight)

$319

Average price (weekend night)

$273
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 85% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chesterton vacation rental deals

  • The best vacation rental properties in Chesterton are Lake Michigan, Indiana Beachfront Vacation Rental (9.9, 23 reviews), Indiana Dunes Downtown 4 Bedroom House Dog Friendly 4 Miles to Beach (9.8, 24), and Your Midwest Dunes Vacation Tri-State Paradise! (9.8, 53), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chesterton, you should consider visiting during the low season. The cheapest vacation homes in Chesterton can be found in November and August.
  • The cheapest night for renting a vacation home in Chesterton is Saturday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chesterton for 24 days.
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FAQs when booking a vacation home in Chesterton

  • What types of vacation rentals are available in Chesterton?

    There are loads of different property types that you can make your vacation home in Chesterton. You’ll find apartments, cabins and houses.

  • Are there any pet-friendly vacation rentals in Chesterton?

    There are a number of dog and pet-friendly Chesterton vacation rentals, with around 22% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Chesterton?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Chesterton?

Our map will help you find the perfect place to stay in Chesterton by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Chesterton

Chesterton vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chesterton. Find cheap vacation homes to rent in Chesterton. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chesterton that suits you best.

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