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Search results; 153 homes in Winchester

Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
,
4.96 out of 5 average rating, 73 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
22–27 Jul
4.92 out of 5 average rating, 176 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 54 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
15–20 Jul
New place to stay
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 191 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 777 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
30 Jul – 4 Aug
4.98 out of 5 average rating, 404 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 103 reviews
Superhost
Cabin in Hillview
Modern-Rustic Cabin, Nature Inspired
2 beds, 1 bathroom
1–6 Oct
4.85 out of 5 average rating, 48 reviews
Bed and breakfast in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
4.8 out of 5 average rating, 5 reviews
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
14–19 Jul
4.82 out of 5 average rating, 139 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jul
4.77 out of 5 average rating, 13 reviews
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
4.92 out of 5 average rating, 87 reviews
Top guest favourite
Home in Mount Sterling
Fully Renovated Uptown Main Street Home
5 bedrooms, 6 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.84 out of 5 average rating, 256 reviews
Top guest favourite
Home in Meredosia
The Fricke Farm
2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Oct
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Beardstown
House of Blessings
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 87 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.82 out of 5 average rating, 184 reviews
Top guest favourite
Holiday home in Meredosia
Scenic 3 bedroom Wildlife Retreat
3 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 96 reviews