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Search results; 156 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
23–28 Aug
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4.92 out of 5 average rating, 183 reviews
Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
4.93 out of 5 average rating, 75 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 197 reviews
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 411 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.91 out of 5 average rating, 108 reviews
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
2 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 783 reviews
Top guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 89 reviews
Flat in Jacksonville
Baker & Birch
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 97 reviews
Guest favourite
Home in Roodhouse
Cozy Corner Bungalow
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 40 reviews
Guest favourite
Home in Beardstown
Nostalgia on 5th St
4 bedrooms, 6 beds, 2 bathrooms
15–20 Aug
4.9 out of 5 average rating, 40 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Home in Carrollton
Sunshine on Fifth
3 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
4.97 out of 5 average rating, 65 reviews
Home in Carrollton
Cozy home in picturesque small town
3 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.82 out of 5 average rating, 185 reviews
Cabin in Pittsfield
Spring Hill Lodge
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
New place to stay
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
16–21 Aug
New place to stay