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Search results; 154 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
9–14 Aug
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4.93 out of 5 average rating, 174 reviews
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
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
7–12 Jul
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
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
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
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
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
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 3
4.94 out of 5 average rating, 105 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Jul
Top guest favourite
Guest house in Carrollton
Shade Family Inn-Carrollton 2-bedroom Apt
4.98 out of 5 average rating, 123 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Jul
Top guest favourite
Home in Mount Sterling
Cozy Cottage 405
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Jul
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
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
4.91 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 Jul
Flat in Jacksonville
Baker & Birch
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
3–8 Jul
Top guest favourite
Home in Carrollton
Sunshine on Fifth
4.97 out of 5 average rating, 64 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
4.98 out of 5 average rating, 317 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
21–26 Jul
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 2
4.9 out of 5 average rating, 97 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Jul