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Search results; 225 homes in Winchester

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Guest favourite
Tiny home in Winchester
Highland Hideout
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.91 out of 5 average rating, 47 reviews
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Top guest favourite
Rooms in Winchester
Shady Grace Equine B&B
3 bedrooms, 3 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Winchester
Welcome to Dancing Deer Acres!
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 68 reviews
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Home in Sardinia
Private 20 Acres|Pets| Hot Tub + Sauna Sleeps 11
4 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 244 reviews
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Guest favourite
Home in Sardinia
Bradford Paradise
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.97 out of 5 average rating, 38 reviews
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Superhost
Home in Winchester
Quiet Farm Escape | Fishing, Nature & Views
3 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
New place to stay
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Guest favourite
Cottage in West Union
Lucky Hooks
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 87 reviews
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Top guest favourite
Farm stay in Hillsboro
A relaxing farmhouse getaway in the country.
4 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 93 reviews
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Superhost
Cabin in West Union
Griffis Game Hunting and Getaway
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 53 reviews
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Top guest favourite
Cabin in Seaman
Amish-built cabin on pond/amazing view!
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.98 out of 5 average rating, 103 reviews
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Top guest favourite
Cabin in West Union
"Clover" 1830s Cabin on Hills Fork Farm
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Sardinia
30 Acre Retreat: Pond, Hot Tub, Disc Golf & More!
5 bedrooms, 8 beds, 3 bathrooms
4–9 Nov
5.0 out of 5 average rating, 37 reviews
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Cabin in Peebles
Stream View Cabin near Serpents Mound
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.52 out of 5 average rating, 82 reviews
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Top guest favourite
Cabin in Seaman
Cozy, Amish-built cabin/amazing sunset view!
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 69 reviews
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Cabin in West Union
Hiking, Amish and fire pits.
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.83 out of 5 average rating, 6 reviews
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Guest favourite
Home in West Union
Finding Grace
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Hillsboro
Ponds, Trails & Pub Room Fun: Hillsboro Getaway
6 bedrooms, 11 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 19 reviews
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Cabin in West Union
Hidden Hills Cabin & Barn Farm Retreat
1 bed, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Hillsboro
Highland Homestead
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 reviews