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 WiFi. Prices start at $131 per night, and houses and cabins are popular options for a stay in Chesterton. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chesterton
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Destination guide

Travel to tranquil Chesterton

The riverfront, beaches and lake display a scene truly unique to Chesterton. This relaxing city is known for its coffeehouses, bird watching and shopping. 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.

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 2021 property listings offer a large selection of 809 vacation rentals around Chesterton. From 740 house rentals to 132 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Chesterton?

Yes, of course. Vrbo has 740 Houses in Chesterton. Our other popular types of vacation rentals in Chesterton include:

  • Cabins: 132 rentals available
  • Cottages: 132 rentals available
  • Condos/Apartments: 49 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Chesterton?

Yes, you can select your preferred vacation rental with pool among our 277 vacation rentals with pool available in Chesterton. Please use our search bar to access the selection of vacation rentals available.