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Search results; 158 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, 183 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
4.93 out of 5 average rating, 75 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
17–22 Aug
New place to stay
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 Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 197 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 411 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 108 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 783 reviews
Top guest favourite
Home in Meredosia
The Fricke Farm
2 bedrooms, 3 beds, 1.5 bathrooms
30 Nov – 5 Dec
4.98 out of 5 average rating, 61 reviews
Guest favourite
Flat in Carrollton
Farmhouse Loft
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.85 out of 5 average rating, 195 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
Flat in Jacksonville
Baker & Birch
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
18–23 Aug
New place to stay
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 432 reviews
Guest favourite
Flat in Mount Sterling
Quiet and Cozy
1 bedroom, 1 double bed, 1 bathroom
17–22 Aug
4.86 out of 5 average rating, 7 reviews
Hotel room in Jacksonville
2 Queen Beds | Super 8 Jacksonville | Family Stay
1 bedroom, 2 queen beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 89 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.87 out of 5 average rating, 55 reviews
Guest favourite
Home in Beardstown
The Ole Pizza Place
2 bedrooms, 3 beds, 1 bathroom
2–7 Oct
4.93 out of 5 average rating, 67 reviews