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Search results; 153 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
19–24 Jul
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4.96 out of 5 average rating, 191 reviews
Guest favourite
Loft in Winchester
Loft above a bike and coffee shop
2 bedrooms, 5 beds, 1 bathroom
22–27 Jul
4.92 out of 5 average rating, 176 reviews
Guest favourite
Flat in Winchester
Exposed brick and 10’ ceilings downtown
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 54 reviews
Home in Winchester
1838 home with pond views and kayaking
4 bedrooms, 5 beds, 1 bathroom
16–21 Jul
New place to stay
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
Top guest favourite
Cabin in Jacksonville
Restored 1930s bunkhouse on a hobby farm
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.98 out of 5 average rating, 404 reviews
Home in Alsey
Single-level home with a fireplace and patio
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
4.84 out of 5 average rating, 256 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
Guest favourite
Home in White Hall
Cozy-Rose-Cottage
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
4.92 out of 5 average rating, 87 reviews
Guest favourite
Hotel in Jacksonville
Renovated historic building above a wine bar
1 bedroom, 1 bed, 1 bathroom
18–23 Jul
4.94 out of 5 average rating, 106 reviews
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
15–20 Jul
4.82 out of 5 average rating, 139 reviews
Guest favourite
Home in White Hall
Fire pit and patio near Main Street
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 104 reviews
Top guest favourite
Home in Beardstown
My Little Bungalow on Monroe Street.
2 bedrooms, 5 beds, 1.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 319 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, 429 reviews
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
Guest favourite
Loft in Pittsfield
14-foot ceilings with courthouse views downtown
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 94 reviews
Guest favourite
Home in Jacksonville
Rees Residential
2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Place to stay in Virginia
1850s log cabin overlooking the lake
1 bedroom, 2 queen beds, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 383 reviews