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Search results; 226 homes in Winchester

Guest favourite
Tiny home in Winchester
Highland Hideout
1 bedroom, 1 bed, 1 private bathroom
3–8 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
3–8 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
Top guest favourite
Home in Sardinia
Bradford Paradise
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Home in Winchester
Quiet Farm Escape | Fishing, Nature & Views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
New place to stay
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
Guest favourite
Cabin in Winchester Township
White Pine Cottage-cozy tiny home w/ earthy decor
2 bedrooms, 3 beds, 1 bathroom
28 Oct – 2 Nov
4.97 out of 5 average rating, 140 reviews
Top guest favourite
Cabin in Seaman
Amish-built cabin on pond/amazing view!
2 bedrooms, 3 beds, 1 bathroom
7–12 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
6–11 Sept
4.98 out of 5 average rating, 66 reviews
Guest favourite
Home in West Union
Finding Grace
1 bedroom, 1 queen bed, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Cabin in West Union
Griffis Game Hunting and Getaway
2 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.86 out of 5 average rating, 51 reviews
Guest favourite
Cottage in West Union
Lucky Hooks
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 87 reviews
Top guest favourite
Farm stay in Hillsboro
A relaxing farmhouse getaway in the country.
4 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 90 reviews
Guest favourite
Cabin in Peebles
Hunter Lodge (Pine Valley Cabins)
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Hillsboro
Ponds, Trails & Pub Room Fun: Hillsboro Getaway
6 bedrooms, 11 beds, 3.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Cabin in Peebles
Deer Lodge At Pine Valley Cabins
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.86 out of 5 average rating, 70 reviews
Top guest favourite
Cabin in West Union
Fox Den Private Couples getaway
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Sardinia
30 Acre Retreat: Pond, Hot Tub, Disc Golf & More!
5 bedrooms, 8 beds, 3 bathrooms
3–8 Nov
5.0 out of 5 average rating, 35 reviews
Cabin in Peebles
Stream View Cabin near Serpents Mound
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.52 out of 5 average rating, 81 reviews