Viewed on an early Spring day, a wooden staircase along a sandy hillside at Indiana Dunes National Park, near Chesterton, IN.

Search Chesterton Cottage Rentals

  • 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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chesterton cottages

House (4 Bedrooms) | Front of property

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 ￥43,516
￥97,518 total
includes taxes & fees
Jun 30 - Jul 1
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Property grounds

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
New Buffalo
9.8 out of 10, Exceptional, (202 reviews)
"Great weekend getaway! Clean comfy house, responsive host, and overall a fabulous stay!"
United States
Halima
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
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.
The price is ￥33,295
￥82,888 total
includes taxes & fees
Jun 30 - Jul 1
Treehouse Bungalow- Quaint and Cozy Getaway!
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, (50 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is ￥58,013
￥105,325 total
includes taxes & fees
Jun 27 - Jun 28
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Beach nearby, sun loungers, beach towels

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Miller Beach
10.0 out of 10, Exceptional, (51 reviews)
"Had a great stay and robin was super helpful and friendly! Great location close to lake"
United States
Weylin W.
The price is ￥101,915
￥169,043 total
includes taxes & fees
Jul 18 - Jul 19
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
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, (19 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.
The price is ￥43,473
￥81,440 total
includes taxes & fees
Jul 6 - Jul 7
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
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)
"Incredibly clean. LOVE THAT"
United States
Matthew M.
The price is ￥152,711
￥174,550 total
includes taxes & fees
Jun 30 - Jul 1
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Terrace/patio

Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (93 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 ￥137,318
￥232,471 total
includes taxes & fees
Jun 28 - Jun 29
Private Beach Steps to the Lake.
House (Multiple Bedrooms) | Interior

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
3.0 star property
La Porte
The price is ￥138,475
￥231,577 total
includes taxes & fees
Jul 26 - Jul 27
Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
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

Spring House Inn

Spring House Inn

8/10 Good
"Older property that once was quite upscale. It has an interesting history. The room was clean, staff did their jobs, breakfast was minimal. The hotel shows its age and needs maintenance and upgrades."
William 1-night trip
Posted 1 hour ago
Spring House Inn

Find out more about Chesterton

Chesterton Cottages information

Number of reviews
439
Accommodation
99 Cottages
Lowest Price
￥81,440
Highest Price
￥232,471

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.