A wooden staircase ascending a sandy hill with sparse vegetation.

Search Chesterton Cottage Rentals from CA $600

  • 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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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 CA $411
CA $840 total
includes taxes & fees
Sep 27 - Sep 28
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, (59 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is CA $198
CA $600 total
includes taxes & fees
Sep 7 - Sep 8
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, (55 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is CA $374
CA $744 total
includes taxes & fees
Sep 7 - Sep 8
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, (15 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 CA $300
CA $652 total
includes taxes & fees
Sep 15 - Sep 16
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 CA $831
CA $950 total
includes taxes & fees
Sep 16 - Sep 17
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 CA $900
CA $1,677 total
includes taxes & fees
Sep 16 - Sep 17
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

Best Western Indian Oak

Best Western Indian Oak

8/10 Good
"Good hot breakfast. Nice patio attached to the room for watching the sunset and listening to the night sounds."
Linda 1-night trip
Posted 1 hour ago
Best Western Indian Oak

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
252
Accommodation
97 Cottages
Lowest Price
CA $600
Highest Price
CA $1,677

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.

Explore a world of travel with Expedia