A wooden staircase ascending a sandy hill with sparse vegetation.

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$301 nightly
The price is $337
Oct 1 - Oct 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.
$480 nightly
The price is $538
Oct 1 - Oct 2
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.
$429 nightly
The price is $441
Oct 6 - Oct 7
Total with taxes and fees
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.

4. 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 1 - Oct 2
Total with taxes and fees
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.

5. 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.
$1,095 nightly
The price is $1,095
Oct 5 - Oct 6
Total with taxes and fees
Private Beach Steps to the Lake.
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
"Love this casino and hotel."
John 2-night trip
Posted 1 hour ago
Blue Chip Casino Hotel and Spa

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
123
Accommodation
95 Cottages
Lowest Price
$337
Highest Price
$1,095

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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