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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
14–19 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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Guest favourite
Home in Chatfield
Convenient, Family friendly!
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 75 reviews
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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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Top 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
4.94 out of 5 average rating, 100 reviews
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Home in Harmony
Harmony Home w/ Fire Pit: 5 Mi to Niagara Cave!
5 bedrooms, 8 beds, 2 bathrooms
19–24 Oct
4.85 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Decorah
Rustic Acres Cabin & Springs
4 bedrooms, 8 beds, 3 bathrooms
15–20 Nov
4.97 out of 5 average rating, 261 reviews
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Superhost
Home in Le Roy
Benton House (pet friendly, low fees, greenhouses)
2 bedrooms, 2 beds, 1 bathroom
3–8 Jan
4.64 out of 5 average rating, 11 reviews
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Top guest favourite
Cabin in Wykoff
Rochester Luxury Log cabin Whispering Oaks Retreat
6 bedrooms, 17 beds, 2.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 89 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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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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Home in Rochester
Charming Century Home Walk to Mayo
3 bedrooms, 4 beds, 2 bathrooms
29 Nov – 4 Dec
New place to stay
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Top guest favourite
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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Top guest favourite
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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Home in Spring Valley
Midcentury Modern by winery, Mayo, Bluff Country
3 bedrooms, 10 beds, 2.5 bathrooms
5–10 Oct
4.79 out of 5 average rating, 175 reviews
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Guest favourite
Home in Rochester
Spacious park-side home, close to Mayo Clinic
5 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.82 out of 5 average rating, 79 reviews
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Superhost
Farm stay in Spring Valley
Valley Angus Farmhouse
7 bedrooms, 20 beds, 1.5 bathrooms
1–6 Oct
4.75 out of 5 average rating, 65 reviews
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Guest favourite
Guest house in Cresco
The Blonde, The Beard, & The Bee N Bee
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Decorah
Driftless Retreat | Sleeps 13 | Near Decorah
4 bedrooms, 9 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 19 reviews