A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesterton cottages

A two-story house with a stone chimney, a brick exterior, and a front porch with a bench.

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
The price is ￥46,763
￥95,519 total
includes taxes & fees
Sep 27 - Sep 28
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
A covered outdoor seating area with a sofa, two chairs, and a coffee table.

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.
The price is ￥22,531
￥50,630 total
includes taxes & fees
Sep 27 - Sep 28
Treehouse Bungalow- Quaint and Cozy Getaway!
A two-story building with a balcony, a front door, and a sign that reads 'Sweet Inn.'

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, (59 reviews)
The price is ￥42,512
￥84,646 total
includes taxes & fees
Sep 28 - Sep 29
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

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.
The price is ￥38,575
￥76,316 total
includes taxes & fees
Oct 7 - Oct 8
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.

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 ￥94,470
￥108,011 total
includes taxes & fees
Sep 27 - Sep 28
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.

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.
The price is ￥86,598
￥172,723 total
includes taxes & fees
Oct 7 - Oct 8
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

Furness Mansion

Furness Mansion

8/10 Good
"Nice place, cozy room. Near a noisy road and railroad - hard to ignore on the deck, but easy to ignore from our room. A part was missing from TV so it wouldn’t work. Help coming ‘soon’ meant 4 hours before a second TV was brought in. Polite but slow response and have seen no sign of the promised discount. But they did ask the maid to bring a box of microwave popcorn for us. Nice to be close to Indiana Dunes."
Andrea 1-night trip
Posted 4 hours ago
Furness Mansion

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
139
Accommodation
97 Cottages
Lowest Price
￥50,630
Highest Price
￥172,723

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.