A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chesterton cottages

House (4 Bedrooms) | Front of property

1. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
3.0 star property
Chesterton
$542 nightly
The price is $607
Sep 27 - Sep 28
Total with taxes and fees
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Property grounds

2. 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.
$285 nightly
The price is $319
Sep 21 - Sep 22
Total with taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Exterior

3. 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, (58 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
$455 nightly
The price is $510
Sep 21 - Sep 22
Total with taxes and fees
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Exterior

4. 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, (16 reviews)
"We loved this property!"
United States
Robin L.
$429 nightly
The price is $440
Sep 30 - Oct 1
Total with taxes and fees
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to 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.
$650 nightly
The price is $650
Sep 21 - Sep 22
Total with taxes and fees
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, (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 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

Spring House Inn

Spring House Inn

8/10 Good
"Convenient"
David 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
$607
Highest Price
$607

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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