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Search results; 290 homes in Chesterfield

Guest favourite
Home in Chesterfield
The Chesterfield Farmhouse on 35 acres
2 bedrooms, 4 beds, 2 private bathrooms
14–19 Jul
,
4.92 out of 5 average rating, 73 reviews
Top guest favourite
Home in Medora
country living
2 bedrooms, 3 beds, 1 bathroom
7–12 Jul
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Room in Carlinville
Spacious family bedroom in Victorian Rt 66 home
3 beds, 1.5 bathrooms
1–6 Jul
4.92 out of 5 average rating, 49 reviews
Guest favourite
Bungalow in Carlinville
The Carlinville Sunset Bungalow
3 bedrooms, 3 beds, 3 bathrooms
9–14 Jul
4.98 out of 5 average rating, 41 reviews
Guest house in Plainview
Sip & Stay Vineyard Getaway
3 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Carlinville
The Carlinville Cottage
3 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
4.96 out of 5 average rating, 49 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.82 out of 5 average rating, 184 reviews
Top guest favourite
Cabin in Brighton
Log Cabin with Breathtaking View
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.97 out of 5 average rating, 110 reviews
Dome in Worden
Family Dome | Hot Tub | Farm Fun Near St. Louis
1 bedroom, 5 beds, No bathroom
2–7 Jul
New place to stay
Top guest favourite
Cabin in Piasa
Oak Rest Cabin
3 bedrooms, 4 beds, 2 bathrooms
28 Jul – 2 Aug
4.88 out of 5 average rating, 17 reviews
Guest favourite
Home in Carlinville
Victorian Home on Rt. 66
4 bedrooms, 6 beds, 1.5 bathrooms
13–18 Jul
4.99 out of 5 average rating, 76 reviews
Guest favourite
Home in Staunton
2br home, private yard hot tub
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
4.87 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Carrollton
The Charleston Suite
3 bedrooms, 6 beds, 1 bathroom
2–7 Jul
4.98 out of 5 average rating, 54 reviews
Guest favourite
Room in Carlinville
Charming private room in shared house on Rt. 66
1 queen bed, 1.5 bathrooms
1–6 Jul
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Jerseyville
McClusky Trail Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
4.95 out of 5 average rating, 83 reviews
Guest favourite
Home in Carlinville
Historic Home near Blackburn & Square 2 King beds
2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
4.92 out of 5 average rating, 83 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
4.91 out of 5 average rating, 102 reviews
Top guest favourite
Flat in Jerseyville
Luxury loft
2 bedrooms, 4 beds, 2 bathrooms
28 Jul – 2 Aug
4.97 out of 5 average rating, 94 reviews
Dome in Worden
Family Dome | Hot Tub | Farm Fun Near St. Louis
1 bedroom, 2 queen beds, No bathroom
2–7 Jul
New place to stay