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Search results; 225 homes in Chesterfield

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Top guest favourite
Home in Chesterfield
The Chesterfield Farmhouse on 35 acres
2 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.92 out of 5 average rating, 78 reviews
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Home in Greenfield
The Shed House- Beautiful Sunsets on 14 Acres
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 70 reviews
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Room in Carlinville
Charming private room in shared house on Rt. 66
1 queen bed, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 51 reviews
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Home in Medora
country living
2 bedrooms, 3 beds, 1 bathroom
16–21 Nov
4.87 out of 5 average rating, 69 reviews
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Flat in Litchfield
The State Street Loft II | Downtown Retreat
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 9 reviews
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Flat in Carlinville
The Rustic Modern Loft | Carlinville Square
2 bedrooms, 2 beds, 1 bathroom
7–12 Nov
4.81 out of 5 average rating, 21 reviews
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Home in Carlinville
The Carlinville Cottage
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
4.96 out of 5 average rating, 54 reviews
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Home in Virden
Private indoor pool with custom lighting
5 bedrooms, 25 beds, 2.5 bathrooms
12–17 Oct
4.77 out of 5 average rating, 304 reviews
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Bungalow in Carlinville
The Carlinville Sunset Bungalow
3 bedrooms, 3 beds, 3 bathrooms
12–17 Oct
4.98 out of 5 average rating, 46 reviews
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Home in Elsah
Elsah’s Finn Inn- restaurant across street
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.94 out of 5 average rating, 116 reviews
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Guest house in Plainview
Sip & Stay Vineyard Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 9 reviews
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Guest house in Carlinville
ThE HiDeAwAy
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 164 reviews
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Top guest favourite
Home in Litchfield
Harrison House; PETS WELCOME; FENCED YARD
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 321 reviews
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Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
1 bedroom, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 432 reviews
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Home in Carlinville
The Campground House
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.97 out of 5 average rating, 122 reviews
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Room in Carlinville
Spacious family bedroom in shared Victorian home
3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 54 reviews
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Top guest favourite
Cabin in Brighton
Log Cabin with Breathtaking View
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 117 reviews
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Flat in Litchfield
The State Street Loft | Small Town Charm
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 39 reviews
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Home in Florissant
Secluded Property w Pool and Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
4–9 Oct
4.82 out of 5 average rating, 28 reviews