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Search results; 222 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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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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Home in Carlinville
Historic Home near Blackburn & Square 2 King beds
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 86 reviews
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Top guest favourite
Guest house in Carlinville
ThE HiDeAwAy
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 166 reviews
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Guest house in Plainview
Sip & Stay Vineyard Getaway
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Home in Carlinville
Victorian Home on Rt. 66
4 bedrooms, 6 beds, 1.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 77 reviews
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Guest favourite
Home in Staunton
2br home, private yard hot tub
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.88 out of 5 average rating, 157 reviews
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Top guest favourite
Cabin in Brighton
Log Cabin with Breathtaking View
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 119 reviews
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Top guest favourite
Room in Carlinville
Spacious family bedroom in shared Victorian home
3 beds, 1.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 55 reviews
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Top guest favourite
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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Superhost
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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Superhost
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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Superhost
Apartment in Grafton
Timber Ridge Retreat 319B |2BR/2BA Grafton Getaway
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
New place to stay
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Dome in Worden
Family Dome: Hot Tub, Farm Fun, Brewery & Pizza
1 bedroom, 2 queen beds, No bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Dome in Worden
Romantic Dome: Private Hot Tub + Brewery & Pizza
1 bedroom, 1 king bed, No bathroom
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Flat in Litchfield
The State Street Loft | Small Town Charm
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 39 reviews
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Tiny home in Carlinville
Timberline Ridge-Tiny Piney
1 bedroom, 2 queen beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Godfrey
Aunt M's Place
3 bedrooms, 3 beds, 1 bathroom
9–14 Nov
4.94 out of 5 average rating, 187 reviews