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Search results; 160 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
7–12 Sept
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 75 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 Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 198 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, 67 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
24–29 Oct
4.97 out of 5 average rating, 787 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, 413 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.91 out of 5 average rating, 112 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Carrollton
The Charleston Suite
3 bedrooms, 6 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 56 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
4.81 out of 5 average rating, 27 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.82 out of 5 average rating, 185 reviews
Room in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bed, 1.5 bathrooms
7–12 Sept
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
7–12 Sept
4.74 out of 5 average rating, 23 reviews
Superhost
Cottage in Hamburg
Calhoun Cottage
4 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.83 out of 5 average rating, 77 reviews
Top guest favourite
Home in Mount Sterling
Fully Renovated Uptown Main Street Home
5 bedrooms, 6 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 33 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway Lower Lodge
4 bedrooms, 8 beds, 2 bathrooms
8–13 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
4.91 out of 5 average rating, 102 reviews