A wooden staircase ascending a sandy hill with sparse vegetation.

Search Chesterton Cottage Rentals from CA $745

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chesterton cottages

House (4 Bedrooms) | Front of property

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
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
House (4 Bedrooms) | Interior

2. Stroll to Shore! Michigan City Family Getaway

Stroll to Shore! Michigan City Family Getaway
3.0 star property
Michigan City
The price is CA $899
CA $1,488 total
includes taxes & fees
Aug 12 - Aug 13
Stroll to Shore! Michigan City Family Getaway
House (4 Bedrooms) | Interior

3. 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 CA $321
CA $782 total
includes taxes & fees
Aug 5 - Aug 6
Group-friendly Michigan City Home Near Beach!
House (3 Bedrooms) | Front of property

4. 2 Mi to Beach! Michigan City Hot Tub Haven

2 Mi to Beach! Michigan City Hot Tub Haven
3.0 star property
Michigan City
The price is CA $322
CA $745 total
includes taxes & fees
Aug 23 - Aug 24
2 Mi to Beach! Michigan City Hot Tub Haven
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

10/10 Excellent
"Love the outdoor pool & bar. Very clean and the pool was nice & warm."
Christina 2-night trip
Posted 11 hours ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
2
Accommodation
99 Cottages
Lowest Price
CA $745
Highest Price
CA $1,488

Frequently asked questions

Why book your cottage in Chesterton with Expedia?
Booking a cottage in Chesterton is as simple as deciding on your travel dates and picking an ideal place for a vacation in the outdoors. From chic retreats to low-cost properties and cottages that have perks like a hot tub, Expedia has something for all styles and tastes. As for irresistible deals? We have them too!
How can I find cheap cottages in Chesterton?
With Expedia's convenient filter tool, sourcing cheap cottages in Chesterton has never been easier. To discover properties that are very pocket friendly, narrow your search results by star rating, amenities and budget.
What is there to do in Chesterton near my cottage?
Whatever you love to do, Chesterton has lots of things to keep you going. Indiana Dunes State Park, Dune Acres Beach and Coffee Creek Watershed Conservancy Preserve are on most travelers' to-do lists. Don't leave without exploring Lustron House, Chellberg Farm and Cowles Bog Trailhead either. With Expedia's hotel deals in Chesterton, you can discover even more wonderful attractions like these with the cash you save.

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