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Search results; 153 homes in Winchester

Flat in Winchester
The Primrose inside historic commercial bldg
2 bedrooms, 3 beds, 1 private bathroom
7–12 Aug
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4.96 out of 5 average rating, 73 reviews
Guest favourite
Loft in Winchester
The Bike Flat
4.92 out of 5 average rating, 182 reviews, 2 bedrooms, 5 beds, 1 bathroom
16–21 Aug
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
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, 408 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Home in Alsey
Douglas Street Retreat
4.8 out of 5 average rating, 15 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Aug
Top guest favourite
Flat in Murrayville
Peace on the Prairie - Studio Apartment
4.97 out of 5 average rating, 432 reviews, 1 bedroom, 4 beds, 1 bathroom
1–6 Sept
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
23–28 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
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
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
Cabin in Jacksonville
Audrey's Abode
4.97 out of 5 average rating, 780 reviews, 2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
Guest favourite
Home in White Hall
The Humble Hideaway
4.92 out of 5 average rating, 106 reviews, 3 bedrooms, 3 beds, 2 bathrooms
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
Rooms in Pittsfield
Sloth Lodging (Upper Level)
4.91 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Home in Pittsfield
Newly remodeled home
4.87 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
4.91 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug