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Search results; 152 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
22–27 Jul
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4.92 out of 5 average rating, 177 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
4.89 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
17–22 Jul
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
4.96 out of 5 average rating, 191 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Home in Pittsfield
Florence Guest House
4.84 out of 5 average rating, 256 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 404 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Home in Alsey
Douglas Street Retreat
4.79 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jul
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 777 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
4.82 out of 5 average rating, 139 reviews, 1 bedroom, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 104 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
4.92 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
4.92 out of 5 average rating, 39 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Jul
Superhost
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4.79 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
18–23 Jul
Guest favourite
Home in Jacksonville
Rees Residential
4.85 out of 5 average rating, 46 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Barn in Jacksonville
Basketball Pickleball +Party Room + Loft Sleeps 17
4.97 out of 5 average rating, 97 reviews, 2 bedrooms, 16 beds, 1.5 bathrooms
20–25 Jul
Flat in Jacksonville
Baker & Birch
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Home in Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!
4.84 out of 5 average rating, 32 reviews, 4 bedrooms, 13 beds, 2.5 bathrooms
18–23 Aug