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Search results; 147 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
23–28 Aug
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4.92 out of 5 average rating, 182 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
7–12 Aug
4.93 out of 5 average rating, 74 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
6–11 Aug
New place to stay
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 195 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.98 out of 5 average rating, 408 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.97 out of 5 average rating, 780 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.92 out of 5 average rating, 106 reviews
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
2 queen beds, 1.5 bathrooms
25–30 Aug
4.95 out of 5 average rating, 211 reviews
Top guest favourite
Home in Meredosia
The Fricke Farm
2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Oct
4.98 out of 5 average rating, 61 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.8 out of 5 average rating, 15 reviews
Superhost
Cabin in Hillview
Modern-Rustic Cabin, Nature Inspired
2 beds, 1 bathroom
4–9 Aug
4.86 out of 5 average rating, 49 reviews
Flat in Carrollton
Farmhouse Loft
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.85 out of 5 average rating, 191 reviews
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 95 reviews
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 97 reviews
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.92 out of 5 average rating, 88 reviews
Top guest favourite
Cottage in Beardstown
The Jungle Farm Country Quiet, Town Convenient
3 bedrooms, 4 beds, 2 bathrooms
6–11 Dec
4.94 out of 5 average rating, 77 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
16–21 Aug
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Cabin in Carrollton
Graham Farm Cabin
2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
4.93 out of 5 average rating, 150 reviews