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Search results; 162 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
15–20 Nov
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4.92 out of 5 average rating, 186 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
12–17 Sept
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
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.93 out of 5 average rating, 75 reviews
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 199 reviews
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, 787 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
13–18 Sept
4.9 out of 5 average rating, 39 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 415 reviews
Top guest favourite
Home in Carrollton
Sunshine on Fifth
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.97 out of 5 average rating, 68 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 113 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.8 out of 5 average rating, 15 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
4.84 out of 5 average rating, 256 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.91 out of 5 average rating, 93 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 22 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.82 out of 5 average rating, 185 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
Guest favourite
Home in Mount Sterling
Fully Renovated Uptown Main Street Home
5 bedrooms, 6 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 33 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
4.81 out of 5 average rating, 27 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway Lower Lodge
4 bedrooms, 8 beds, 2 bathrooms
12–17 Sept
4.89 out of 5 average rating, 9 reviews