We found 762 vacation rentals — enter your dates for availability
COVID-19 advisory
Some properties allow cancellations up to 14 days before arrival. Check the policy before booking. Also, we strongly recommend following guidance from health officials as well as travel advisories from local authorities. Visit our help article
Discover a selection of 1,000 vacation rentals in Chesterton, IN that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $99 per night, and lodges and houses are popular options for a stay in Chesterton. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find the best place to stay — Chesterton
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Activities
Activities and attractions in Chesterton
Are you hoping to find things to do during your stay? Venture out of your cozy vacation rental and check out everything that Chesterton has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:
- Washington Park Zoo (11.7 mi / 18.9 km)
- Deep River Water Park (12.7 mi / 20.5 km)
- Legacy Hills Golf Club (15.8 mi / 25.4 km)
Weather
Seasonal weather averages in Chesterton
If you're hoping to enjoy some warm-weather activities on your vacation, July, June, August and September are the hottest months to visit, when temperatures average 82°F.
Natural features
Exploring the natural landscape of Chesterton
Chesterton is famous for its pristine beaches and panoramic lake views. Whether you're an adventurous traveler or just want to appreciate the scenery, Chesterton is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:
- Indiana Dunes National Lakeshore (3.4 mi / 5.4 km)
- Indiana Dunes State Park (3.9 mi / 6.3 km)
- Marquette Park (10.7 mi / 17.1 km)
How to get there
Transportation to and around Chesterton
The nearest airport is in Chicago, IL (MDW-Midway Intl.), located 37.7 mi (60.6 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Chicago, IL (ORD-O'Hare Intl.), which is 50.9 mi (81.9 km) away.
How many vacation rentals are available around Chesterton, IN?
Our 2020 property listings offer a large selection of 762 vacation rentals around Chesterton. From 2 vacation lodge rentals to 523 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.
What are the popular point of interests near where I can stay when traveling to Chesterton?
Vrbo offers a large selection of vacation rentals near lovely places in Chesterton. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:
- Indiana Dunes State Park: 925 vacation rentals
- Coffee Creek Watershed Conservancy Preserve: 409 vacation rentals
- Lustron House: 408 vacation rentals
- Indiana Dunes National Lakeshore: 492 vacation rentals
- Michigan City Station: 863 vacation rentals
But there are many other points of interest around Chesterton listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.
Can I rent Lodges in Chesterton?
Yes, of course. Vrbo has 2 Lodges in Chesterton. Our other popular types of vacation rentals in Chesterton include:
- Houses: 523 rentals available
- Cabins: 144 rentals available
- Cottages: 144 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.
Can I find a vacation rental with pool in Chesterton?
Yes, you can select your preferred vacation rental with pool among our 255 vacation rentals with pool available in Chesterton. Please use our search bar to access the selection of vacation rentals available.