A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

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

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 €382
includes taxes & fees
1 Sept - 2 Sept
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 €496
includes taxes & fees
2 Sept - 3 Sept
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 €459
includes taxes & fees
23 Aug - 24 Aug
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 €465
includes taxes & fees
28 Aug - 29 Aug
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 €636
includes taxes & fees
9 Sept - 10 Sept
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 €1,256
includes taxes & fees
29 Aug - 30 Aug
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 €916
includes taxes & fees
12 Aug - 13 Aug
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

Spring House Inn

Spring House Inn

8/10 Good
"Cute hotel. Slightly dated but seems like it’s currently being renovated, so no complaints there. The pool area had a fireplace! I wanna go and swim when that’s running! The breakfast left much to be desired. I am vegan and my options were incredibly limited - the oatmeal packets seemed to be out of date (very hard packed seasoning and the oats never really “puffed up”) and I’m used to having peanut butter at hotels to get some protein and they had none. The other people in my group are not vegan and said the breakfast was generally lame. Shared my feelings on peanut butter. I was disappointed bc reviews had specifically mentioned a good breakfast."
Lucy 1-night trip
Posted less than an hour ago
Spring House Inn

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
Accommodation
99 Cottages
Lowest Price
€459
Highest Price
€916

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 holiday 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 travellers' 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.