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Search results; 151 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
22–27 Jul
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4.93 out of 5 average rating, 175 reviews
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
12–17 Jul
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
10–15 Jul
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 73 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
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 403 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Pittsfield
Florence Guest House
4.84 out of 5 average rating, 256 reviews, 3 bedrooms, 5 beds, 2 bathrooms
11–16 Jul
Home in Alsey
Douglas Street Retreat
4.77 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Jul
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 776 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 103 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 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
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
4.92 out of 5 average rating, 87 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 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
Top guest favourite
Home in Mount Sterling
Cozy Cottage 405
4.93 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
4.98 out of 5 average rating, 319 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
21–26 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
18–23 Jul
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
4.94 out of 5 average rating, 31 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 94 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–15 Jul
Flat in Carrollton
Farmhouse Loft
4.85 out of 5 average rating, 190 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug