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Search results; 152 homes in Winchester

Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.96 out of 5 average rating, 194 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 179 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
1 bedroom, 1 queen bed, 1 bathroom
5–10 Aug
4.89 out of 5 average rating, 54 reviews
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
Bunkhouse Seventy-Four
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 406 reviews
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
New place to stay
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.82 out of 5 average rating, 139 reviews
Home in Alsey
Douglas Street Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Aug
4.79 out of 5 average rating, 14 reviews
Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 5 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.84 out of 5 average rating, 256 reviews
Room in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bed, 1.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 94 reviews
Guest favourite
Home in White Hall
The Humble Hideaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 104 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, 779 reviews
Hotel room in Jacksonville
King Bed | Super 8 Jacksonville | Free Breakfast
1 bedroom, 1 bathroom
1–6 Aug
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
2 queen beds, 1.5 bathrooms
11–16 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Home in Carrollton
Sunshine on Fifth
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.97 out of 5 average rating, 65 reviews