Chesterton vacation rentals

We found 1,312 vacation rentals — enter your dates for availability

Discover a selection of 29 homes and other vacation rentals in Chesterton that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll have the amenities you expect and more, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
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  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
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Tranquil Chesterton will entice you

The riverfront, beaches and lake are a perfect backdrop to your vacation home in Chesterton. Travelers to this relaxing city praise the coffeehouses, bird watching and shopping. Take in top local attractions like Indiana Dunes National Park and Lake Michigan. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chesterton

Do you want to find attractions to visit in the city? Venture out of your vacation home and experience everything that Chesterton has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Washington Park Zoo (11.6 mi / 18.6 km)
  • Oasis Splash Pad (11.6 mi / 18.7 km)
  • The Course at Aberdeen (11.9 mi / 19.1 km)
  • Deep River Water Park (12.9 mi / 20.8 km)
  • Albanese Candy Factory (14.4 mi / 23.2 km)
  • Shady Creek Winery (14.5 mi / 23.3 km)

Exploring the natural landscape of Chesterton

Travelers enjoy Chesterton for its beaches and lakeside setting. Whether you're an outdoor enthusiast or just want to take in the scenery, Chesterton is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Indiana Dunes National Park (2.7 mi / 4.3 km)
  • Indiana Dunes Visitor Center (1.7 mi / 2.7 km)
  • Coffee Creek Watershed Conservancy Preserve (2.5 mi / 4 km)
  • Dune Acres Beach (3.5 mi / 5.6 km)
  • Waverly Beach (3.5 mi / 5.7 km)
  • Kemil Beach (5.7 mi / 9.1 km)

Seasonal weather in Chesterton

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

Transportation to and around Chesterton

The nearest airport is in Chicago Midway Airport (MDW), located 37 mi (59.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away.

Frequently asked questions

What is the best area to stay in Chesterton when booking a vacation rental?
Porter is one of the most sought-after neighborhoods to find a Vrbo vacation rental in Chesterton. Pick from our range of relaxing stays and then get out and explore this destination like a local.
What is the most popular type of vacation rental accommodation in Chesterton?
According to our data, cottages are the most popular type of vacation property in Chesterton. But as you know, everyone’s idea of an awesome stay differs. Vrbo has vacation rentals in a variety of shapes and sizes, and we’ll help you find the perfect fit.
How much does it cost to rent a vacation rental in Chesterton?
The average price for a vacation home in Chesterton can vary depending on factors such as length of stay, season and property type. Whether you prefer a sprawling villa with lots of bedrooms or a quaint cottage just enough for two, just enter your travel dates to see stays with terrific value.
How much does it cost to rent a beach house in Chesterton?
Prices for beach houses in Chesterton can vary depending on the style and size of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filters to narrow your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly vacation rentals in Chesterton?
Pack a suitcase for the pup in your life because Chesterton has 22 vacation homes that put out the welcome mat to pets. Let your happy hound have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Chesterton?
Grab your swimsuit and goggles, because there are two houses with a private pool in Chesterton. Base yourself at one of these popular vacation homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Chesterton?
Some of the most popular rental amenities people are searching for in Chesterton are a water view, a garden and a beach view. Whether you’re vacationing with family, your besties or even pets, Vrbo vacation properties come with the best amenities for beginning new traditions with the people you love.
Are there large group vacation rentals in Chesterton?
You can pick from three vacation properties in Chesterton that can sleep 10 or more guests. Whether you’re organizing a trip with extended family or some kind of special event, there’s enough room to get your favorite people together under the same roof.
Are there vacation rentals in Chesterton that welcome kids?
Chesterton has 22 family-friendly vacation rentals to pick from. And finding a stay that welcomes children is super easy with Vrbo’s “Properties good for families” filter. Besides having the entire place to yourselves, you can also look forward to amenities and perks such as bunk beds, yards and private pools.
What are the top attractions for families in Chesterton?
There are plenty of amazing things to do and see with the family in Chesterton, such as:

  • Indiana Dunes State Park
  • Indiana Dunes Visitor Center
  • Dune Acres Beach

Can I find two-bedroom vacation rentals in Chesterton?
Gather your family and experience complete comfort and privacy in one of the three two-bedroom vacation homes Chesterton has to offer.
Are there vacation rentals with WiFi in Chesterton?
You can pick from 12 vacation rentals with WiFi in Chesterton. If you’d like to disconnect from daily life on your escape, but still need to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Chesterton?
There are 21 vacation homes with air conditioning in Chesterton offering that cooling breeze and extra comfort level. Just enter your preferred travel dates and then take advantage of our filter tool to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in Chesterton?
The minimum required age is usually 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Chesterton vacation rental before booking your trip.
How long can I rent a vacation rental in Chesterton for?
It really depends on the Chesterton property. To look over a list of options offering extended stays, simply type your travel dates and number of people into Vrbo. You can look forward to having the entire property to yourself, as well as amenities such as a kitchen, air conditioning and outdoor spaces where the kids can run and play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Chesterton?
Weekend break or extended escape, Vrbo has some incredible bargains and discounts in Chesterton that’ll suit your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — at an affordable rate.

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