Search Vacation Homes in Chesterton
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 754 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)

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

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, (83)

Modern Farmhouse steps from downtown! Here comes summer!
Modern Farmhouse steps from downtown! Here comes summer!
10.0 out of 10, Exceptional, (161)

cozy home with hot tub next to downtown Valparaiso
cozy home with hot tub next to downtown Valparaiso
10.0 out of 10, Exceptional, (59)

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)

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
9.0 out of 10, Wonderful, (57)
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.
Save an average of 15% on thousands of hotels when you're signed in
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, (85)
The price is SAR 806
SAR 1,273 total
includes taxes & fees
30 Mar - 31 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 255
SAR 370 total
includes taxes & fees
26 Mar - 27 Mar

The Neighborhood Hotel - Grand Beach
The Neighborhood Hotel - Grand Beach
9.4 out of 10, Exceptional, (40)
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

Holiday Inn Express & Suites Michigan City by IHG
5/5 Excellent
Loved it
"I very much liked the hotel. Friendly and helpful staff, very clean, bright and cheerfully decorated, comfortable bed and bedding, good breakfast choices. I will definitely stay there again. "
A verified traveler stayed at Holiday Inn Express & Suites Michigan City by IHG
Posted 20 hours ago