Chesterton holiday rentals

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

Discover a selection of 31 homes and other holiday rentals in Chesterton that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a fireplace and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Relaxing Chesterton will entice you

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

Sightseeing in and around Chesterton

Are you hoping to discover attractions to see in the city? Venture out of your holiday home and experience everything that makes Chesterton a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers enjoy Chesterton for its beaches and lakeside setting. Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chesterton. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Kemil Beach (5.7 mi / 9.1 km)
  • Dunbar Beach (6 mi / 9.7 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 21°C.

Transport to and around Chesterton

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Chesterton?
According to our research, houses are the most sought-after type of holiday property in Chesterton. But that goes without saying, everyone’s idea of an epic trip isn’t the same. Stayz has holiday homes of all sizes, shapes and budgets, so you’re bound to find the perfect fit for you.
How much does it cost to rent a holiday home in Chesterton?
Length of stay, property type and season are some of the things that can affect the price of a holiday home. Simply click on your dates of travel to find your ideal match. From comfy cottages to expansive villas, all Stayz holiday homes provide amazing value.
How much does it cost to rent a beach house in Chesterton?
Prices for beach houses in Chesterton may vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Stayz and how many guests to view your holiday home options and prices. From there you can use our filter tool to tailor your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Chesterton?
Yes. You’ll have a choice of 17 holiday homes that roll out the welcome mat in Chesterton on Stayz. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Spot can join in the fun.
What are popular home amenities in Chesterton?
Some of the most popular home amenities people are searching for in Chesterton include a barbecue grill, nearby museums and a garden. Whether you’re hitting the road with family, buddies or even pets, Stayz holiday homes come with the best amenities for hanging out with the people you love.
Are there large group holiday homes in Chesterton?
With 11 Chesterton holiday homes that can host a group of five or more people, you can bring a few extra pals or family members along. Whether you’re planning an informal get-together or a birthday party, Stayz will help you find a comfy space for the occasion.
Are there holiday homes in Chesterton that welcome kids?
Gather your whole family for a fun-packed adventure in Chesterton at one of our 17 family-friendly holiday properties. Many of these stays come with amenities that are ideally suited to getaways with children, including kitchens, living rooms and entertainment units. Simply check the “Properties good for families” filter box and pick out your favourite.
What are the top attractions for families in Chesterton?
You’ll find loads of exciting things to do and see with the family in Chesterton, including:

  • Lake View Beach
  • Portage Lakefront Beach
  • Dune Acres Beach

Are there one-bedroom holiday homes in Chesterton?
Chesterton has two one-bedroom homes available. Often located in desirable areas due to their smaller size, a one-bedroom holiday home is great if you’re travelling with your partner or a buddy. And with home comforts such as full kitchens and more privacy than a standard hotel, you’ll be able to kick back and relax while exploring this awesome destination.
Can I find two-bedroom holiday homes in Chesterton?
You can select from five two-bedroom holiday homes in Chesterton. Settle the kids into the second room or fill it with a couple of your best friends. There’s space for whoever’s lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Chesterton?
There are seven holiday homes with WiFi in Chesterton. If you want to disconnect from the world on your break, 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 Stayz.
How can I find holiday homes with air conditioning in Chesterton?
Chesterton has 17 holiday homes where you can chill out in air-conditioned comfort. To book a property on Stayz that comes with this amenity, enter your dates of travel and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Chesterton?
The minimum age is usually 16, 18 or 21. It can differ from property to property on Stayz, so look at the rules of your chosen Chesterton holiday home before booking your stay.
How long can I rent a holiday home in Chesterton for?
It’s really down to the Chesterton property. To look over a list of options offering extended stays, just type your travel dates and number of people into the Stayz search page. You can enjoy having the entire place to yourself, along with home comforts like a kitchen, air conditioning and outdoor spaces where the kids can run and play. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.

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