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Search results; Over 1,000 homes in Chester

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Top guest favourite
Home in Chester
Cozy 4 bedroom 2 bath Victorian home w/ fireplace
4 bedrooms, 4 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.98 out of 5 average rating, 62 reviews
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Home in Lime Springs
Driftless Area farmhouse 3 bedroom/ 2 bath
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Place to stay in Wykoff
Historic Wykoff Jail Haus
1 bedroom, 1 queen bed, 1 bathroom
10–15 Oct
4.92 out of 5 average rating, 525 reviews
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Farm stay in Spring Valley
Woods Edge Cozy Retreat @Whispering Winds
1 bedroom, 1 double bed, 1 bathroom
16–21 May
4.85 out of 5 average rating, 226 reviews
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Cabin in Spring Valley
Modern Cabin on 28 acres of Valley Views and ponds
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 100 reviews
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Treehouse in Mabel
Nestling Pines Treehouse
2 bedrooms, 1 bed, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 195 reviews
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Home in Alta Vista
Grandma Z's Guesthouse
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Oct
4.93 out of 5 average rating, 139 reviews
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Cabin in McIntire
Bailey Exchange Cottage
1 bedroom, 3 beds, WC
20–25 Sept
3.75 out of 5 average rating, 4 reviews
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Superhost
Flat in Lanesboro
Dog friendly, Upstairs Studio, Apt 2
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
New place to stay
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Home in Harmony
Petra's Garden 2
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Lanesboro
Boho Vibes, bring your dog!
2 bedrooms, 3 beds, 1 bathroom
22–27 Oct
4.97 out of 5 average rating, 61 reviews
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Superhost
Farm stay in Spring Valley
Valley Angus Farmhouse
7 bedrooms, 20 beds, 1.5 bathrooms
24–29 Sept
4.75 out of 5 average rating, 64 reviews
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Home in Rose Creek
6 Unique Church Home Destination Stay
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 45 reviews
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Place to stay in Houston
Owl's Nest Lodge
1 bedroom, 3 beds, 1.5 bathrooms
21–27 Sept
New place to stay
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Top guest favourite
Home in Mabel
Cozy Oak Street Cottage
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 42 reviews
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Cabin in Osage
Experience Log cabin Living
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.82 out of 5 average rating, 160 reviews
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Guest favourite
Home in Preston
Root Haven
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 12 reviews
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Barn in Dorchester
The Barn Loft
4 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 168 reviews
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Cabin in Calmar
Buffalo Lodge
1 bedroom, 3 beds, WC
20–25 Sept
4.99 out of 5 average rating, 276 reviews