A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 ￥19,826
￥45,104 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥37,084
￥73,541 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥99,415
￥107,973 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥87,164
￥173,853 total
includes taxes & fees
Nov 9 - Nov 10
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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Top Chesterton Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"There was plenty of free parking. The rooms were nice sized snd clean. The staff was friendly. We would stay here again if we were in the area for sure."
stuart 1-night trip
Posted less than an hour ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
123
Accommodation
95 Cottages
Lowest Price
￥45,104
Highest Price
￥173,853

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.