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Compare 635 Vacation Homes in Chesterton with updated reviews, rates, and availability.

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, (180)

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
10.0 out of 10, Exceptional, (82)

Journey To Valpo | Home Near Downtown!
Journey To Valpo | Home Near Downtown!
9.8 out of 10, Exceptional, (22)

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

"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
10.0 out of 10, Exceptional, (70)

Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly
Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly
9.8 out of 10, Exceptional, (10)

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)

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, (78)
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

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, (83)
The price is SAR 750
SAR 1,197 total
includes taxes & fees
12 Mar - 13 Mar

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, (51)
The price is SAR 296
SAR 416 total
includes taxes & fees
13 Mar - 14 Mar

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
9.8 out of 10, Exceptional, (51)
The price is SAR 319
SAR 1,165 total
includes taxes & fees
16 Mar - 17 Mar
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

Baymont by Wyndham New Buffalo
3/5 Okay
"Michigan is wonderful the hotel lobbiest was amazing with a great pool accomodations. Our bathroom sink handle came off and there was no screen in our window. "
A verified traveler stayed at Baymont by Wyndham New Buffalo
Posted 13 hours ago