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Search results; 220 homes in Chesterfield

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Guest favourite
Home in Chesterfield
The Chesterfield Farmhouse on 35 acres
2 bedrooms, 4 beds, 2 private bathrooms
30 Sept – 5 Oct
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4.92 out of 5 average rating, 76 reviews
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Home in Medora
country living
2 bedrooms, 3 beds, 1 bathroom
17–22 Sept
4.87 out of 5 average rating, 68 reviews
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Guest house in Plainview
Sip & Stay Vineyard Getaway
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Greenfield
The Shed House- Beautiful Sunsets on 14 Acres
2 bedrooms, 3 beds, 1 bathroom
10–15 Nov
4.97 out of 5 average rating, 70 reviews
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Top guest favourite
Bungalow in Carlinville
The Carlinville Sunset Bungalow
3 bedrooms, 3 beds, 3 bathrooms
2–7 Sept
4.98 out of 5 average rating, 45 reviews
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Home in Staunton
2br home, private yard hot tub
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.88 out of 5 average rating, 155 reviews
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Room in Grafton
The Deckhouse at Aerie's Resort
2 king beds, 1 bathroom
1–6 Sept
4.92 out of 5 average rating, 25 reviews
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Home in Carlinville
Victorian Home on Rt. 66
4 bedrooms, 6 beds, 1.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 76 reviews
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Home in Carlinville
The Campground House
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
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
1–6 Sept
4.92 out of 5 average rating, 53 reviews
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Home in Carlinville
Historic Home near Blackburn & Square 2 King beds
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.92 out of 5 average rating, 86 reviews
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Superhost
Home in Virden
Private indoor pool with custom lighting
5 bedrooms, 25 beds, 2.5 bathrooms
14–19 Sept
4.76 out of 5 average rating, 302 reviews
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Superhost
Home in Florissant
Secluded Property w Pool and Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
4.81 out of 5 average rating, 26 reviews
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Dome in Worden
Romantic Dome: Private Hot Tub + Brewery & Pizza
1 bedroom, 1 king bed, No bathroom
12–17 Sept
5.0 out of 5 average rating, 4 reviews
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Room in Carlinville
Quiet Victorian hideaway on Rt 66
1 double bed, 1.5 bathrooms
1–6 Sept
4.97 out of 5 average rating, 65 reviews
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Cabin in Brighton
Log Cabin with Breathtaking View
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.97 out of 5 average rating, 117 reviews
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Tiny home in Carlinville
Timberline Ridge-Tiny Piney
1 bedroom, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 28 reviews
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Dome in Worden
Glamping Dome: Hot Tub, Brewery & Romantic Escape
1 bedroom, 1 king bed, No bathroom
7–12 Sept
4.8 out of 5 average rating, 5 reviews
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Home in Jerseyville
McClusky Trail Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 89 reviews