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Search results; 214 homes in Chesterfield

Guest favourite
Home in Chesterfield
The Chesterfield Farmhouse on 35 acres
2 bedrooms, 4 beds, 2 private bathrooms
3–8 Aug
,
4.92 out of 5 average rating, 74 reviews
Guest favourite
Home in Medora
country living
4.88 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Top guest favourite
Room in Carlinville
Spacious family bedroom in Victorian Rt 66 home
4.92 out of 5 average rating, 50 reviews, 3 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Bungalow in Carlinville
The Carlinville Sunset Bungalow
4.98 out of 5 average rating, 44 reviews, 3 bedrooms, 3 beds, 3 bathrooms
20–25 Jul
Guest favourite
Room in Carlinville
Quiet Victorian hideaway on Rt 66
4.97 out of 5 average rating, 62 reviews, 1 double bed, 1.5 bathrooms
20–25 Jul
Guest house in Plainview
Sip & Stay Vineyard Getaway
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Cabin in Piasa
Oak Rest Cabin
4.88 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Jul – 2 Aug
Guest favourite
Tiny home in Carlinville
Timberline Ridge-Tiny Piney
5.0 out of 5 average rating, 27 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Staunton
2br home, private yard hot tub
4.87 out of 5 average rating, 145 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Home in Carrollton
Cozy home in picturesque small town
4.82 out of 5 average rating, 184 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Guest house in Carlinville
ThE HiDeAwAy
4.98 out of 5 average rating, 154 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Home in Mount Olive
Relaxing Fishing Cabin
4.92 out of 5 average rating, 77 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
Guest favourite
Flat in Litchfield
The State Street Loft | Small Town Charm
5.0 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Jul
Top guest favourite
Cabin in Brighton
Log Cabin with Breathtaking View
4.97 out of 5 average rating, 112 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Farm stay in Carrollton
Peaceful Country Stay- The Carrollton Farmhouse
5.0 out of 5 average rating, 50 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Flat in Bunker Hill
The Loft
4.98 out of 5 average rating, 66 reviews, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Carlinville
Historic Home near Blackburn & Square 2 King beds
4.92 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Flat in Jerseyville
Luxury loft
4.97 out of 5 average rating, 96 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Home in Carlinville
The Carlinville Cottage
4.96 out of 5 average rating, 50 reviews, 3 bedrooms, 6 beds, 2 bathrooms
6–11 Aug