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Search results; 153 homes in Winchester

Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 bed, 1 private bathroom
5–10 Aug
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4.89 out of 5 average rating, 54 reviews
Guest favourite
Loft in Winchester
The Bike Flat
4.92 out of 5 average rating, 182 reviews, 2 bedrooms, 5 beds, 1 bathroom
16–21 Aug
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Aug
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
4.96 out of 5 average rating, 194 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 406 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Home in Alsey
Douglas Street Retreat
4.8 out of 5 average rating, 15 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Aug
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 779 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Guest favourite
Home in White Hall
The Humble Hideaway
4.92 out of 5 average rating, 106 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
New place to stay, 1 bed, 1.5 bathrooms
16–21 Aug
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
4.94 out of 5 average rating, 32 reviews, 2 bedrooms, 4 beds, No bathroom
9–14 Aug
Home in Pittsfield
Newly remodeled home
4.87 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
4.92 out of 5 average rating, 88 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Home in Jacksonville
Rees Residential
4.85 out of 5 average rating, 48 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
4.92 out of 5 average rating, 39 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Beardstown
House of Blessings
4.99 out of 5 average rating, 91 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4.89 out of 5 average rating, 37 reviews, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug