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Search results; 154 homes in Winchester

Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 bed, 1 private bathroom
7–12 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
5–10 Jul
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 72 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
Superhost
Flat in Carrollton
Farmhouse Loft
4.85 out of 5 average rating, 188 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 775 reviews, 2 bedrooms, 4 beds, 1 bathroom
8–13 Jul
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 402 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 102 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Home in Pittsfield
Florence Guest House
4.85 out of 5 average rating, 254 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 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
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
4–9 Jul
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
Loft in Pittsfield
Historic Loft on Adams
4.9 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in Meredosia
The Fricke Farm
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Home in Mount Sterling
Fully Renovated Uptown Main Street Home
5.0 out of 5 average rating, 28 reviews, 5 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
Home in Alsey
Douglas Street Retreat
4.83 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
Top guest favourite
Home in Beardstown
House of Blessings
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
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