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Search results; 161 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
15–20 Sept
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4.97 out of 5 average rating, 200 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
15–20 Nov
4.93 out of 5 average rating, 187 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
15–20 Sept
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
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
6–11 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
27 Sept – 2 Oct
4.98 out of 5 average rating, 415 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 White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 114 reviews
Top guest favourite
Treehouse in Annada
“Exclusive” River Cabin on Stilts (3 bedroom)
3 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.9 out of 5 average rating, 92 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
16–21 Dec
4.9 out of 5 average rating, 40 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
4.81 out of 5 average rating, 27 reviews
Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bedroom, 1 bed, 1.5 bathrooms
20–25 Sept
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
4.8 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Carrollton
The Charleston Suite
3 bedrooms, 6 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 57 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
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
15–20 Sept
4.74 out of 5 average rating, 23 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.91 out of 5 average rating, 93 reviews
Superhost
Cottage in Hamburg
Calhoun Cottage
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.83 out of 5 average rating, 77 reviews