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Search results; 153 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.96 out of 5 average rating, 191 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
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
15–20 Jul
New place to stay
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
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 73 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
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
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
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
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 103 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 Beardstown
My Little Bungalow on Monroe Street.
2 bedrooms, 5 beds, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 319 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
20–25 Jul
4.92 out of 5 average rating, 39 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
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.85 out of 5 average rating, 46 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 21 reviews
Flat in Carrollton
Farmhouse Loft
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.85 out of 5 average rating, 190 reviews
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
2 queen beds, 1.5 bathrooms
11–16 Aug
4.95 out of 5 average rating, 208 reviews
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 3
1 bedroom, 1 bed, 1 bathroom
18–23 Jul
4.94 out of 5 average rating, 106 reviews