A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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, (60 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is AU$465
includes taxes & fees
1 Nov - 2 Nov
Treehouse Bungalow- Quaint and Cozy Getaway!
A two-story building with a balcony, a front door, and a sign that reads 'Sweet Inn.'

2. Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Michigan City
9.6 out of 10, Exceptional, (59 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is AU$747
includes taxes & fees
9 Oct - 10 Oct
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Quintessential lake cottage

3. 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 AU$670
includes taxes & fees
21 Oct - 22 Oct
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to 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 AU$1,555
includes taxes & fees
14 Oct - 15 Oct
Private Beach Steps to the Lake.
A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

5. 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)
"Perfect stay! The house was spotless, stylish, and located perfectly. Tori was incredibly responsive. Highly recommended"
United States
kimberly b.
The price is AU$959
includes taxes & fees
12 Oct - 13 Oct
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo 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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Nice"
jack 1-night trip
Posted 2 hours ago
Blue Chip Casino Hotel and Spa

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
123
Accommodation
97 Cottages
Lowest Price
AU$465
Highest Price
AU$1,555

Frequently asked questions

How much do cottages in Chesterton cost?
Expect to pay between AU$465 and AU$1,555 per night for cottages in Chesterton. No matter your budget, a wonderful stay is only a few clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What is there to do in Chesterton near my cottage?
Whatever you love doing, Chesterton has tons to keep you occupied. Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach are on many visitors' to-do lists. Don't leave without exploring Portage Lakefront Beach, Dune Acres Beach and Kemil Beach either. With Expedia's hotel deals in Chesterton, you'll be able to see even more neat attractions like these with the cash you save.