A wooden staircase ascending a sandy hill with sparse vegetation.

Search Cottages in Chesterton

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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
The price is AED 1,091
AED 2,228 total
includes taxes & fees
27 Sep - 28 Sep
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.
The price is AED 526
AED 1,239 total
includes taxes & fees
24 Sep - 25 Sep
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, (59 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is AED 992
AED 1,975 total
includes taxes & fees
24 Sep - 25 Sep
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.
The price is AED 731
AED 1,583 total
includes taxes & fees
30 Sep - 1 Oct
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.
The price is AED 2,204
AED 2,520 total
includes taxes & fees
24 Sep - 25 Sep
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.
The price is AED 2,020
AED 4,029 total
includes taxes & fees
5 Oct - 6 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterton Hotel Reviews

Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

10/10 Excellent
"N/A"
James 1-night trip
Posted 11 hours ago
Quality Inn Chesterton near Indiana Dunes National Park I-94

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.