A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chesterton cottages

Property grounds

1. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.8 out of 10, Excellent, (57 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is ￥22,575
￥68,398 total
includes taxes & fees
Sep 7 - Sep 8
Treehouse Bungalow- Quaint and Cozy Getaway!
Exterior

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, (54 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is ￥47,328
￥90,819 total
includes taxes & fees
Sep 2 - Sep 3
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
House (3 Bedrooms) | Front of property

3. 2 Mi to Beach! Michigan City Hot Tub Haven

2 Mi to Beach! Michigan City Hot Tub Haven
3.0 star property
Michigan City
The price is ￥36,127
￥83,692 total
includes taxes & fees
Aug 23 - Aug 24
2 Mi to Beach! Michigan City Hot Tub Haven
Smart TV

4. Brand New Cottage Walkable to All Downtown Michigan City & Beach!

Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Michigan City
9.8 out of 10, Exceptional, (21 reviews)
"Great house, great location! "
United States
Alexis L.
The price is ￥47,170
￥85,695 total
includes taxes & fees
Aug 28 - Aug 29
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Terrace/patio

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 ￥103,648
￥118,477 total
includes taxes & fees
Sep 2 - Sep 3
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Terrace/patio

6. Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (96 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 ￥134,096
￥227,017 total
includes taxes & fees
Aug 29 - Aug 30
Private Beach Steps to the Lake.
House (4 Bedrooms) | Interior

7. Stroll to Shore! Michigan City Family Getaway

Stroll to Shore! Michigan City Family Getaway
3.0 star property
Michigan City
The price is ￥100,966
￥167,120 total
includes taxes & fees
Aug 12 - Aug 13
Stroll to Shore! Michigan City Family Getaway
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
"We stayed in a junior suite for two nights and the room was big, comfortable, and clean. We enjoyed the pool, even though it was small. We saw the hot tub after the fact and would have used it had we known how that worked with guests because it was in a gazebo quite a ways from the pool area. We had room service for breakfast and our order didn’t get picked up but arrived quickly after we called. The staff were friendly and accommodating. We would definitely stay again."
Candy 2-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
Accommodation
99 Cottages
Lowest Price
￥83,692
Highest Price
￥167,120

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.