A wooden staircase ascending a sandy hill with sparse vegetation.

Search Chesterton Cottages

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chesterton cottages

A covered outdoor seating area with a sofa, two chairs, and a coffee table.

1. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (62 reviews)
"We loved our accommodations and the host is wonderful!"
United States
Unspecified U.
$260 nightly
The price is $291
Nov 15 - Nov 16
Total with taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Ceiling fans keep air flow and also Central Air and Heat.

2. 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, (19 reviews)
"Great location, clear communication about check-in/check-out, plenty of space, and the right amenities!"
United States
Kelley P.
$464 nightly
The price is $478
Nov 15 - Nov 16
Total with taxes and fees
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
A wooden deck with a bench and two chairs, overlooking a body of water and trees.

3. Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (97 reviews)
"The property and host was amazing. The property was steps from the beach and amazing sunsets. The property was clean and very pet friendly. Went to the beach every day and enjoyed every moment. John, was uplifting and a perfect host. Plan to go back next year. Thank you for a wonderful couple of days."
United States
Marilee J.
$1,097 nightly
The price is $1,097
Nov 15 - Nov 16
Total with taxes and fees
Private Beach Steps to the Lake.
A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

4. 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)
"Super nice place.!!!"
United States
Citlaly D.
$681 nightly
The price is $681
Nov 15 - Nov 16
Total with taxes and fees
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
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

Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Room was clean with a beautiful view though it was too cold to sit outside and enjoy it. Breakfast was average. Make your own waffles, scrambled eggs and sausage links or patties every day and then the norm toast,bagels muffins, fruit, juice and coffee. Hotel was great and workers were amazing."
Wretha 3-night trip
Posted 16 hours ago
Best Western Indian Oak

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
142
Accommodation
95 Cottages
Lowest Price
$291
Highest Price
$1,097

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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