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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chesterton vacation rentals

Front of property

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

Group-friendly Michigan City Home Near Beach!

Group-friendly Michigan City Home Near Beach!
3.0 star property
Michigan City
10.0 out of 10, Exceptional, (2 reviews)
"This was exactly what we needed for our little family getaway. The only thing was there was very little parking and make sure to not park in the alley right next to the house as the neighbor will ask you to move. "
United States
Hannah
The price is P14,163
P34,505 total
includes taxes & fees
Aug 5 - Aug 6
Group-friendly Michigan City Home Near Beach!
Interior

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
3.0 star property
La Porte
Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
Interior

Stroll to Shore! Michigan City Family Getaway

Stroll to Shore! Michigan City Family Getaway
3.0 star property
Michigan City
The price is P39,581
P65,515 total
includes taxes & fees
Jul 29 - Jul 30
Stroll to Shore! Michigan City Family Getaway
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

Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

8/10 Good
"The property is an older one. It looks like they are actively working on up grading it. The front desk attendant, we believe to be the owner, was very nice and helpful throughout our stay. The room was very, very clean. I was actually surprised because the hallway had a mildewy odd kind of smell. The carpet was pieced together. We did not smell it in the room. The air conditioning was good. I cannot comment on the breakfast because we went closer to the marina area to a coffee shop. The location was very close, but not walkable to the marina/beach area. I would stay there again."
Sharon 1-night trip
Posted less than an hour ago
Baymont by Wyndham New Buffalo

Find out more about Chesterton

Search for holiday rentals in Chesterton on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterton using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesterton!

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.

How many vacation rentals are there in Chesterton?

Choose from 35 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 Indiana Dunes State Park and Lustron House.

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.