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Search results; 161 homes in Winchester

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Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
15–20 Nov
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4.93 out of 5 average rating, 187 reviews
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Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds
17–22 Sept
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Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed
6–11 Oct
4.89 out of 5 average rating, 54 reviews
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Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 75 reviews
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Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed
26 Sept – 1 Oct
4.97 out of 5 average rating, 200 reviews
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Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds
28 Sept – 3 Oct
4.75 out of 5 average rating, 16 reviews
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Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 786 reviews
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Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds
18–23 Sept
4.84 out of 5 average rating, 256 reviews
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Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.98 out of 5 average rating, 415 reviews
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Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 114 reviews
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Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds
18–23 Sept
4.81 out of 5 average rating, 140 reviews
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Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds
18–23 Sept
4.91 out of 5 average rating, 93 reviews
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Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds
18–23 Sept
4.96 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 102 reviews
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Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds
18–23 Sept
4.9 out of 5 average rating, 42 reviews
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Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 2
1 bedroom, 1 bed
1–6 Nov
4.88 out of 5 average rating, 104 reviews
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Top guest favourite
Home in Meredosia
The Fricke Farm
2 bedrooms, 3 beds
7–12 Dec
4.98 out of 5 average rating, 61 reviews
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Top guest favourite
Guest house in Carrollton
Shade Family Inn-Carrollton 2-bedroom Apt
2 bedrooms, 2 queen beds
19–24 Sept
4.98 out of 5 average rating, 132 reviews
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Cabin in Pittsfield
Spring Hill Lodge
2 bedrooms, 3 beds
17–22 Sept
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