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Search results; 234 homes in Winchester

Guest favourite
Tiny home in Winchester
Highland Hideout
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.91 out of 5 average rating, 46 reviews
Top guest favourite
Rooms in Winchester
Shady Grace Equine B&B
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
4.98 out of 5 average rating, 54 reviews
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
Guest favourite
Home in Sardinia
Bradford Paradise
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.97 out of 5 average rating, 37 reviews
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
Superhost
Home in Winchester
Quiet Farm Escape | Fishing, Nature & Views
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
New place to stay
Top guest favourite
Cabin in Seaman
Amish-built cabin on pond/amazing view!
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 103 reviews
Top guest favourite
Cabin in West Union
"Clover" 1830s Cabin on Hills Fork Farm
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Cottage in West Union
Lucky Hooks
3 bedrooms, 4 beds, 1 bathroom
12–17 Sept
4.93 out of 5 average rating, 87 reviews
Guest favourite
Cabin in Peebles
Hunter Lodge (Pine Valley Cabins)
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.94 out of 5 average rating, 35 reviews
Guest favourite
Cabin in Peebles
Bunk House (Pine Valley Cabins)
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.94 out of 5 average rating, 51 reviews
Superhost
Cabin in West Union
Griffis Game Hunting and Getaway
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 52 reviews
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, 92 reviews
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, 36 reviews
Top guest favourite
Cabin in Seaman
Cozy, Amish-built cabin/amazing sunset view!
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Home in Dover
Kenyatucky! For your stay or event!
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.88 out of 5 average rating, 26 reviews
Guest favourite
Home in West Union
Finding Grace
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 13 reviews
Cabin in Peebles
Stream View Cabin near Serpents Mound
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.52 out of 5 average rating, 82 reviews
Top guest favourite
Cabin in Peebles
Meadow View Cabin
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 54 reviews