Search Chesterton Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Chesterton cottages

Property grounds

Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (55 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
$428 nightly
The price is $479
May 5 - May 6
Total with taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Terrace/patio

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, (24 reviews)
"great time had by all"
United States
Elliot S.
$686 nightly
The price is $686
May 5 - May 6
Total with taxes and fees
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Exterior

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, (49 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
$627 nightly
The price is $702
May 21 - May 22
Total with taxes and fees
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Smart TV

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, (16 reviews)
"Cute place, extremely clean, comfortable and well-outfitted. It's very convenient, with easy parking and great proximity to downtown Michigan City. "
United States
Heather O.
$277 nightly
The price is $310
May 10 - May 11
Total with taxes and fees
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Exterior

3BR 2b New Buffalo cottage steps to Shopping, Breweries, Beach - pets +NotreDame

3BR 2b New Buffalo cottage steps to Shopping, Breweries, Beach - pets +NotreDame
Downtown New Buffalo
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at the Little Fox Lake Cottage. The location is incredibly convenient—close to everything you need while still feeling like a relaxing getaway. The hosts were fantastic: friendly, responsive, and very easy to communicate with from start to finish.The cottage itself was exactly what we were hoping for—clean, comfortable, and well cared for. It made for the perfect spot to unwind and enjoy some time away. We would definitely stay here again!"
United States
Kara O.
$414 nightly
The price is $425
May 5 - May 6
Total with taxes and fees
3BR 2b New Buffalo cottage steps to Shopping, Breweries, Beach - pets +NotreDame
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

10/10 Excellent
"Wasn’t helped when told about the cold water and no soaps in the rooms bathroom. Took 30 minutes for staff to answer phone Breakfast was limited. A lot of construction."
Christian 2-night trip
Posted 2 hours ago
Best Western Indian Oak

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
92
Accommodation
89 Cottages
Lowest Price
$310
Highest Price
$702

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