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Search results; Over 1,000 homes in Chesterton

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Guest favourite
Bungalow in Chesterton
Charming Country Cottage
2 bedrooms, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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4.98 out of 5 average rating, 129 reviews
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Guest favourite
Home in Chesterton
Downtown Chesterton "Grant-Cottage"
2 bedrooms, 3 beds
13–18 Oct
4.9 out of 5 average rating, 152 reviews
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Flat in Chesterton
Newly Redone Dunes Getaway
2 bedrooms, 2 beds
25–30 Sept
4.76 out of 5 average rating, 17 reviews
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Superhost
Home in Chesterton
Chesterton Ranch with Huge Yard
3 bedrooms, 4 beds
18–23 Oct
New place to stay
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Superhost
Home in Chesterton
Dunes Home – Walk to Town, Fenced Yard, Near Dunes
3 bedrooms, 8 beds
27 Sept – 2 Oct
4.79 out of 5 average rating, 128 reviews
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Superhost
Home in Chesterton
Roomy Retreat–Family&Friends|2 King Beds|Game Room
5 bedrooms, 13 beds
27 Sept – 2 Oct
4.8 out of 5 average rating, 105 reviews
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Home in Chesterton
Small town charm
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.82 out of 5 average rating, 11 reviews
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Top guest favourite
Flat in Chesterton
Chesterton Charmer: Lower Unit
3 bedrooms, 3 beds
20–25 Sept
4.96 out of 5 average rating, 82 reviews
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Guest favourite
Flat in Chesterton
Chesterton Charmer: Upper Unit
2 bedrooms, 4 beds
23–28 Sept
4.93 out of 5 average rating, 71 reviews
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Top guest favourite
Guest house in Chesterton
"myhathouse" detached studio downtown Chesterton
1 bedroom, 2 beds
5–10 Nov
4.92 out of 5 average rating, 422 reviews
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Guest favourite
Guest house in Chesterton
Country Retreat
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 112 reviews
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Guest favourite
Home in Chesterton
The Tower Haus | Dune Trails + Hot Tub
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Chesterton
Retro 1950s Estate w Hot Tub Near Indiana Dunes
4 bedrooms, 7 beds
20–25 Sept
4.98 out of 5 average rating, 101 reviews
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Superhost
Townhouse in Chesterton
South Shore Escape
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.76 out of 5 average rating, 67 reviews
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Guest favourite
Home in Porter
The Porter Nook | Walk to Trails + Dining
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 45 reviews
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Superhost
Home in Porter
Blue Birdhouse - Indiana Dunes
2 bedrooms, 5 beds
27 Sept – 2 Oct
4.89 out of 5 average rating, 136 reviews
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Guest favourite
Townhouse in Chesterton
The Book Nook 2 BDRM
2 bedrooms, 2 beds
17–22 Sept
4.92 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Chesterton
Hotel Whiskey
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 186 reviews
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Superhost
Home in Chesterton
Close to the Dunes State Park!
2 bedrooms, 2 beds
19–24 Sept
4.75 out of 5 average rating, 24 reviews