A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chesterton vacation rentals

A two-story house with a stone chimney, a brick exterior, and a front porch with a bench.

1. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
3.0 star property
Chesterton
The price is CA $409
CA $835 total
includes taxes & fees
Sep 3 - Sep 4
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A modern living room with a grey sofa, a dining table with chairs, a kitchen area with white cabinets, and a TV mounted on the wall.

2. Michigan City Home w/ Hot Tub: 2 Mi to Beach!

Michigan City Home w/ Hot Tub: 2 Mi to Beach!
3.0 star property
Michigan City
The price is CA $280
CA $691 total
includes taxes & fees
Aug 23 - Aug 24
Michigan City Home w/ Hot Tub: 2 Mi to Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterton Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

8/10 Good
"We did really like our stay at the hotel. The room was clean and stocked. We loved the orange citrus smell of their signature toiletries. One of the bed pillows unfortunately was covered with dark disgusting stains and put into a pillow case for my bed. The layout was a bit strange. It was inconvenient to get to the pool from the hotel. We did really love the hot tub area. It felt secluded and relaxing. The tub could have been turned up a few more degrees and the bubbles were nonexistent. It was a short drive to New Buffalo beach which we appreciated. In all we still liked it and will definitely be back. All the employees were extremely helpful, pleasant, and professional."
Karey 1-night trip
Posted 1 hour ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Everything you need to know about Chesterton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton vacation rentals we have selected for you start as low as CA $214 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterton rentals

At Expedia, we put the best Chesterton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Chesterton?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Chesterton, or you can choose a more secluded option if you're looking for relaxation. Discover why Chesterton is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

What's the top vacation rental that Chesterton has to offer?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated vacation home rental in Chesterton offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Chesterton?

Choose from 32 Expedia vacation rentals in Chesterton for a memorable vacation.

What can I see and do in Chesterton?

Indiana Dunes National Park and Lake Michigan are a couple of scenic spots to enjoy the outdoors, whereas Chesterton Art Center is one of the cultural attractions. Other places in town to visit include Lustron House and Indiana Dunes Visitor Center.

What are vacation rentals like in Chesterton?

Vacation rentals are private properties you can reserve for a couple days or more in Chesterton. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family getaway.