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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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Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 75 reviews
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Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
6–11 Oct
4.89 out of 5 average rating, 54 reviews
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Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
20–25 Sept
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Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 200 reviews
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Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.75 out of 5 average rating, 16 reviews
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Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 114 reviews
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Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.84 out of 5 average rating, 257 reviews
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Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 786 reviews
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Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 415 reviews
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Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.74 out of 5 average rating, 23 reviews
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Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 93 reviews
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Home in Jacksonville
Home in Jacksonville, Illinois
3 bedrooms, 6 beds, 1.5 bathrooms
11–16 Oct
4.67 out of 5 average rating, 6 reviews
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Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.86 out of 5 average rating, 51 reviews
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Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.81 out of 5 average rating, 140 reviews
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Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.82 out of 5 average rating, 185 reviews
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Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds, 2 bathrooms
3–8 Oct
4.91 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
2 bedrooms, 5 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 336 reviews
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Home in Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, 13 beds, 2.5 bathrooms
10–15 Dec
4.84 out of 5 average rating, 37 reviews