Photo by Susan Ross

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chesterton cottages

A covered outdoor seating area with a sofa, two chairs, and a coffee table.

1. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (62 reviews)
"We loved our accommodations and the host is wonderful!"
United States
Unspecified U.
The price is €257
includes taxes & fees
9 Nov - 10 Nov
Treehouse Bungalow- Quaint and Cozy Getaway!
Ceiling fans keep air flow and also Central Air and Heat.

2. 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (18 reviews)
"Great property with excellent location to all downtown activities as well as the beach."
United States
christian s.
The price is €418
includes taxes & fees
9 Nov - 10 Nov
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

3. Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
New Buffalo
10.0 out of 10, Exceptional, (26 reviews)
"Super nice place.!!!"
United States
Citlaly D.
The price is €609
includes taxes & fees
9 Nov - 10 Nov
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
A wooden deck with a bench and two chairs, overlooking a body of water and trees.

4. Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (97 reviews)
"Great stay for a week by the beach with family! Perfect location to walk right down to the beach each day. Excited to come back one day!"
United States
Jalen W.
The price is €994
includes taxes & fees
9 Nov - 10 Nov
Private Beach Steps to the Lake.
A single-story house with a front porch, a small deck, and a pathway leading to the door.

5. Cozy Fall Retreat w/ Hot Tub & Fire Pit

Cozy Fall Retreat w/ Hot Tub & Fire Pit
3.0 star property
Michigan City
Cozy Fall Retreat w/ Hot Tub & Fire Pit
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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Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic city centre, while nearby beaches provide perfect spots for summer swimming and sunset views.

See all hotels in Chesterton
A wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

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 holiday 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 travellers' 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.