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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
15–20 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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Superhost
Flat in Lanesboro
Upstairs Studio Hideout, downtown Lanesboro, Apt 3
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
New place to stay
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Guest favourite
Home in Preston
Root River Retreat
2 bedrooms, 1 bathroom
31 Oct – 5 Nov
4.96 out of 5 average rating, 76 reviews
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Guest favourite
Cabin in Spring Valley
Modern Cabin on 28 acres of Valley Views and ponds
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 101 reviews
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Home in Harmony
Harmony Lighthouse
2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Place to stay in Wykoff
Historic Wykoff Jail Haus
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 526 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, 227 reviews
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Home in Rose Creek
6 Unique Church Home Destination Stay
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 45 reviews
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Home in Stewartville
Stewartville Charmer 4/2 by Park, 8 min to airport
4 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 131 reviews
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Home in Alta Vista
The Recker House
5 bedrooms, 5 queen beds, 2.5 bathrooms
16–21 Oct
4.87 out of 5 average rating, 143 reviews
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Home in Harmony
Petra's Garden 2
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Farm stay in Wykoff
Bin There, Done That (and Pickleball too!)
2 bedrooms, 5 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Decorah
Silver Creek Retreat
2 bedrooms, 4 beds, 2.5 bathrooms
16–21 Oct
5.0 out of 5 average rating, 126 reviews
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Cabin in McIntire
Bailey Exchange Cottage
1 bedroom, 3 beds, WC
1–6 Oct
3.75 out of 5 average rating, 4 reviews
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Cabin in Osage
Experience Log cabin Living
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 161 reviews
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Home in Rochester
Nice house near airport and shopping center
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.9 out of 5 average rating, 48 reviews
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Barn in Dorchester
The Barn Loft
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 168 reviews
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Home in Ossian
Enjoy your stay at the "Owl's Nest" Updated Barn
5 bedrooms, 18 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 49 reviews