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Search results; 154 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
13–18 Jul
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4.96 out of 5 average rating, 190 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 174 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
5–10 Jul
New place to stay
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, 72 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
7–12 Jul
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
8–13 Jul
4.97 out of 5 average rating, 775 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
4.91 out of 5 average rating, 102 reviews
Top guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
4.85 out of 5 average rating, 254 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 402 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Jul
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Home in Mount Sterling
Cozy Cottage 405
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 14 reviews
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 3
1 bedroom, 1 bed, 1 bathroom
3–8 Jul
4.94 out of 5 average rating, 105 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.92 out of 5 average rating, 38 reviews
Top guest favourite
Guest house in Carrollton
Shade Family Inn-Carrollton 2-bedroom Apt
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Jul
4.98 out of 5 average rating, 123 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
3–8 Jul
4.91 out of 5 average rating, 53 reviews
Flat in Jacksonville
Baker & Birch
2 bedrooms, 3 beds, 1 bathroom
3–8 Jul
New place to stay
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
2 bedrooms, 5 beds, 1.5 bathrooms
21–26 Jul
4.98 out of 5 average rating, 317 reviews
Top guest favourite
Home in Carrollton
Sunshine on Fifth
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.97 out of 5 average rating, 64 reviews
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 2
1 bedroom, 1 bed, 1 bathroom
3–8 Jul
4.9 out of 5 average rating, 97 reviews