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Search results; 147 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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4.92 out of 5 average rating, 177 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 54 reviews
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, 73 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
New place to stay
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 192 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.98 out of 5 average rating, 405 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 777 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.92 out of 5 average rating, 88 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 104 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
19–24 Jul
New place to stay
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
20–25 Jul
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
1 bedroom, 4 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 430 reviews
Guest favourite
Hotel in Jacksonville
Charming downtown hotel above wine bar - Room 3
1 bedroom, 1 bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 106 reviews
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
4.96 out of 5 average rating, 96 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
23–28 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
4.89 out of 5 average rating, 37 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
4.82 out of 5 average rating, 184 reviews
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
4.85 out of 5 average rating, 46 reviews