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Search results; 153 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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4.92 out of 5 average rating, 178 reviews
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
20–25 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
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, 192 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
7–12 Aug
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 777 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Home in Alsey
Douglas Street Retreat
4.79 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Jul
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
4.92 out of 5 average rating, 88 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 104 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
4.98 out of 5 average rating, 320 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
4.92 out of 5 average rating, 39 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Jul
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
4.97 out of 5 average rating, 431 reviews, 1 bedroom, 4 beds, 1 bathroom
21–26 Jul
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
New place to stay, 1 bed, 1.5 bathrooms
26–31 Jul
Superhost
Flat in Pittsfield
Dome View Loft
4.79 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Jul
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
Home in Carrollton
Cozy home in picturesque small town
4.82 out of 5 average rating, 184 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 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
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 3
4.94 out of 5 average rating, 106 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul