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 private pools. Prices start at $123 per night, and houses and cottages are popular options for a stay in Chesterton. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesterton
Destination guide

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. 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.

Things to do

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)
  • 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)
  • Team Combat LIVE (14.4 mi / 23.1 km)

Seasonal weather in Chesterton

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

Natural features

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 Visitor Center (1.7 mi / 2.7 km)
  • Indiana Dunes National Park (2.7 mi / 4.3 km)
  • Indiana Dunes State Park (3.2 mi / 5.2 km)
  • Lake View Beach (6.4 mi / 10.3 km)
  • Ogden Dunes Beach (6.8 mi / 11 km)
  • Beverly Shores Beach (7.2 mi / 11.6 km)
How to get there

Transportation to and around Chesterton

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

What's the best place to stay if you're looking to rent a house for a weekend in or near Chesterton?

A weekend of clean coastal air and chilled-out vibes at Sheridan Beach in Michigan City will do you the world of good. Book a rental home and stay a couple of nights or longer at this breathtaking coastal destination located 11 miles to the northeast of Chesterton.