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Search results; 155 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.96 out of 5 average rating, 194 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
23–28 Aug
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
4.96 out of 5 average rating, 73 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
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
New place to stay
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 Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.84 out of 5 average rating, 256 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
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.82 out of 5 average rating, 139 reviews
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
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Aug
4.8 out of 5 average rating, 15 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 54 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 21 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
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Carlinville
Charming private room in shared house on Rt. 66
1 queen bed, 1.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 48 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.87 out of 5 average rating, 55 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