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Search results; Over 1,000 homes in Chesterton

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Guest favourite
Flat in Chesterton
Chesterton Charmer: Upper Unit
2 bedrooms, 4 beds, 1 private bathroom
4–9 Sept
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4.93 out of 5 average rating, 67 reviews
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Guest favourite
Home in Chesterton
Downtown Chesterton "Grant-Cottage"
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Oct
4.91 out of 5 average rating, 148 reviews
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Guest favourite
Home in Chesterton
Charming Old Town Retreat in the Heart of Duneland
4 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in Chesterton
Dunes Home – Walk to Town, Fenced Yard, Near Dunes
3 bedrooms, 8 beds, 2 bathrooms
14–19 Sept
4.8 out of 5 average rating, 124 reviews
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Flat in Chesterton
Newly Redone Dunes Getaway
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.73 out of 5 average rating, 15 reviews
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Superhost
Home in Chesterton
Roomy Retreat–Family&Friends|2 King Beds|Game Room
5 bedrooms, 13 beds, 3 bathrooms
13–18 Sept
4.79 out of 5 average rating, 102 reviews
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Top guest favourite
Flat in Chesterton
Chesterton Charmer: Lower Unit
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 80 reviews
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Top guest favourite
Home in Chesterton
Chesterton 3 Bedroom Home Away From Home
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
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Superhost
Townhouse in Chesterton
South Shore Escape
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.76 out of 5 average rating, 66 reviews
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Top guest favourite
Home in Chesterton
Retro 1950s Estate w Hot Tub Near Indiana Dunes
4 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 99 reviews
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Guest favourite
Townhouse in Chesterton
The Book Nook 2 BDRM
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 60 reviews
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Home in Chesterton
Small town charm
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.8 out of 5 average rating, 10 reviews
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Townhouse in Chesterton
Cozy Townhome Duplex w/ Modern Vintage Vibe
2 bedrooms, 1.5 bathrooms
18–23 Oct
4.73 out of 5 average rating, 26 reviews
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Top guest favourite
Flat in Portage
Trailside Retreat
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Guest house in Chesterton
Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 105 reviews
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Top guest favourite
Guest house in Chesterton
"myhathouse" detached studio downtown Chesterton
1 bedroom, 2 beds, 1 bathroom
6–11 Oct
4.92 out of 5 average rating, 420 reviews
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Top guest favourite
Home in Chesterton
Hotel Whiskey
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 184 reviews
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Home in Chesterton
Charming Chesterton Home: w/ Idyllic Location!
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.81 out of 5 average rating, 31 reviews
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Top guest favourite
Cottage in Valparaiso
Flint Lake Cottage.
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 626 reviews