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Search results; 148 homes in Winchester

Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 bed, 1 private bathroom
8–13 Jul
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4.89 out of 5 average rating, 54 reviews
Guest favourite
Loft in Winchester
The Bike Flat
4.93 out of 5 average rating, 174 reviews, 2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
10–15 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, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Flat in Carrollton
Farmhouse Loft
4.85 out of 5 average rating, 189 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 403 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 776 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Top guest favourite
Home in Pittsfield
Florence Guest House
4.85 out of 5 average rating, 255 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
Superhost
Cabin in Hillview
Modern-Rustic Cabin, Nature Inspired
4.85 out of 5 average rating, 48 reviews, 2 beds, 1 bathroom
1–6 Oct
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 103 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Home in Alsey
Douglas Street Retreat
4.77 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Jul
Bed and breakfast in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
4.8 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
Home in Carrollton
Cozy home in picturesque small town
4.82 out of 5 average rating, 184 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
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
12–17 Jul
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Sept
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
4.92 out of 5 average rating, 38 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Top guest favourite
Holiday home in Meredosia
Scenic 3 bedroom Wildlife Retreat
4.98 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
4.97 out of 5 average rating, 429 reviews, 1 bedroom, 4 beds, 1 bathroom
12–17 Jul