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Compare 757 Vacation Homes in Chesterton with updated reviews, rates, and availability.

Miller Beach Blue Door By The Shore #2
Miller Beach Blue Door By The Shore #2
10.0 out of 10, Exceptional, (4)

Sweet Stay By-The-Lake in Michigan City with AC, WiFi
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
9.6 out of 10, Exceptional, (7)

Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub
Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub
9.6 out of 10, Exceptional, (36)

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
10.0 out of 10, Exceptional, (183)

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
9.4 out of 10, Exceptional, (51)

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
9.0 out of 10, Wonderful, (20)

Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town
Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town
10.0 out of 10, Exceptional, (80)

Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
9.6 out of 10, Exceptional, (17)
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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Other property types in Chesterton

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
9.0 out of 10, Wonderful, (54)
The price is AED 290
AED 407 total
includes taxes & fees
27 Apr - 28 Apr

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, (94)

The Neighborhood Hotel - Grand Beach
The Neighborhood Hotel - Grand Beach
9.6 out of 10, Exceptional, (46)
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.
Recent reviews of Chesterton hotels
Recent reviews of Chesterton hotels

Waterbird Lakeside Inn
5/5 Excellent
Key card fiasco
"Love staying here. I have stayed here several times because being able to wake up and look out across a lake is just beautiful. It’s instant relaxation.
The hotel is reasonably clean. I could tell that no one had stayed in my room for awhile but I was there in the off season. My only complaint is that I had to keep returning to the front desk because my key card would stop working. Once, twice, okay. After the third time I was not pleased and the fourth time was absolutely ridiculous. Please fix this! I will be back soon to see the turtles…."
A verified traveler stayed at Waterbird Lakeside Inn
Posted 16 hours ago