A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$296 nightly
The price is $332
Nov 1 - Nov 2
Total with taxes and fees
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.
$459 nightly
The price is $514
Oct 8 - Oct 9
Total with taxes and fees
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.
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.
$1,097 nightly
The price is $1,097
Oct 12 - Oct 13
Total with taxes and fees
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.
$686 nightly
The price is $686
Oct 12 - Oct 13
Total with taxes and fees
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

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Spacious rooms with great amenities. Staff was friendly and helpful."
Michele Figiel 1-night trip
Posted 6 hours ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
123
Accommodation
95 Cottages
Lowest Price
$332
Highest Price
$1,097

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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