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Search results; 155 homes in Winchester

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Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.97 out of 5 average rating, 200 reviews
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Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds
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
6–11 Oct
4.89 out of 5 average rating, 54 reviews
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Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds
28 Nov – 3 Dec
4.93 out of 5 average rating, 187 reviews
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Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds
1–6 Oct
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Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds
1–6 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
24–29 Oct
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
4–9 Oct
4.98 out of 5 average rating, 415 reviews
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Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds
1–6 Oct
4.81 out of 5 average rating, 140 reviews
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Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds
6–11 Oct
4.84 out of 5 average rating, 257 reviews
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Top guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds
6–11 Nov
4.91 out of 5 average rating, 115 reviews
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Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds
1–6 Oct
4.74 out of 5 average rating, 23 reviews
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Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds
5–10 Oct
4.87 out of 5 average rating, 52 reviews
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Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds
4–9 Oct
4.91 out of 5 average rating, 93 reviews
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Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds
4–9 Oct
4.9 out of 5 average rating, 42 reviews
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Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds
3–8 Oct
4.91 out of 5 average rating, 47 reviews
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Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds
1–6 Oct
4.96 out of 5 average rating, 98 reviews
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Superhost
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed
16–21 Oct
4.87 out of 5 average rating, 99 reviews
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Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds
10–15 Oct
4.88 out of 5 average rating, 58 reviews