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 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.
Save an average of 15% on thousands of hotels when you're signed in
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
30 Apr - 1 May

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, (95)

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

Four Winds Casino Resort – New Buffalo
5/5 Excellent
"This is a beautiful place to visit and stay. Staff is amazing, great food, lots of game choices and the room we stayed in was very clean! Highly recommend and I will be returning!"
A verified traveler stayed at Four Winds Casino Resort – New Buffalo
Posted 18 hours ago