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Search results; 153 homes in Winchester

Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 179 reviews
Guest favourite
Flat in Winchester
Sugar Shack, a retro studio apartment
4.89 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Aug
Flat in Winchester
The Primrose inside historic commercial bldg
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
4.96 out of 5 average rating, 194 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Jacksonville
Bunkhouse Seventy-Four
4.98 out of 5 average rating, 406 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
4.82 out of 5 average rating, 139 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Home in Alsey
Douglas Street Retreat
4.79 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Aug
Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
4.8 out of 5 average rating, 5 reviews, 1 bed, 1 bathroom
9–14 Aug
Room in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
New place to stay, 1 bed, 1.5 bathrooms
9–14 Aug
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
4.9 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Home in White Hall
The Humble Hideaway
4.91 out of 5 average rating, 105 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 779 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Top guest favourite
Loft in Virginia
Two Doors Down Loft, Virginia-Lincoln territory!
4.95 out of 5 average rating, 210 reviews, 2 beds, 1.5 bathrooms
11–16 Aug
Guest favourite
Home in Pittsfield
Florence Guest House
4.84 out of 5 average rating, 256 reviews, 3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Place to stay in Virginia
Virginia Lake Getaway/Fishing/Hot Tub/Hammock
4.98 out of 5 average rating, 385 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Carrollton
Sunshine on Fifth
4.97 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug