A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesterton cottages

Property grounds

1. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (58 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is £312
includes taxes & fees
7 Sept - 8 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 £423
includes taxes & fees
2 Sept - 3 Sept
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Smart TV

3. 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 £397
includes taxes & fees
28 Aug - 29 Aug
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
House (3 Bedrooms) | Front of property

4. 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 £393
includes taxes & fees
23 Aug - 24 Aug
2 Mi to Beach! Michigan City Hot Tub Haven
Exterior

5. 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, (14 reviews)
"Loved staying in this cottage. Super close to everything, clean and overall in a great location. Hosts were very helpful and easy to communicate with. Highly recommend! Will look to stay here again for sure. "
United States
Miranda S.
The price is £444
includes taxes & fees
2 Sept - 3 Sept
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Terrace/patio

6. 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 £541
includes taxes & fees
9 Sept - 10 Sept
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Terrace/patio

7. 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 £1,073
includes taxes & fees
29 Aug - 30 Aug
Private Beach Steps to the Lake.
House (4 Bedrooms) | Interior

8. Stroll to Shore! Michigan City Family Getaway

Stroll to Shore! Michigan City Family Getaway
3.0 star property
Michigan City
The price is £785
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

Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"It's conveniently located, it's clean, and it's well priced."
rick 2-night trip
Posted 2 hours ago
Best Western Indian Oak

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
Accommodation
98 Cottages
Lowest Price
£393
Highest Price
£785

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.