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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 Spring Valley
Midcentury Modern by winery, Mayo, Bluff Country
3 bedrooms, 10 beds, 2.5 bathrooms
21–26 Sept
4.79 out of 5 average rating, 174 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 Preston
Root River Retreat
2 bedrooms, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 76 reviews
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Guest favourite
Home in Chatfield
Convenient, Family friendly!
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.92 out of 5 average rating, 74 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
5–10 Oct
4.97 out of 5 average rating, 109 reviews
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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
27 Sept – 2 Oct
4.94 out of 5 average rating, 100 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
7–12 Oct
4.99 out of 5 average rating, 89 reviews
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Top guest favourite
Home in Stewartville
Stewartville Charmer 4/2 by Park, 8 min to airport
4 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
4.95 out of 5 average rating, 130 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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Home in Harmony
Petra's Garden
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.79 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Decorah
Silver Creek Retreat
2 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 126 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
4.89 out of 5 average rating, 19 reviews
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Top guest favourite
Farm stay in Cresco
Tailwind Cottage
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 26 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, 11 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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Guest favourite
Guest house in Cresco
The Blonde, The Beard, & The Bee N Bee
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Decorah
Driftless Retreat | Sleeps 13 | Near Decorah
4 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
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