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Search results; Over 1,000 homes in Winchester

Guest favourite
Cottage in Winchester
Carter's Wine Country Luxury Casita
1 bedroom, 1 bed, 1 private bathroom
8–13 Jul
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4.95 out of 5 average rating, 168 reviews
Top guest favourite
Guest suite in Winchester
Ranch/Separate Private 2 Bdrm Suite w/Patio
4.96 out of 5 average rating, 250 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Winchester
Vineyard Poolside Retreat
4.88 out of 5 average rating, 65 reviews, 4 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Superhost
Room in Winchester
Private room/shared bath
4.88 out of 5 average rating, 77 reviews, 1 queen bed, 1 bathroom
12–17 Jul
Top guest favourite
Place to stay in Winchester
Downstairs guestroom with private bathroom
4.9 out of 5 average rating, 540 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Room in Winchester
Cozy Private Casita
4.92 out of 5 average rating, 380 reviews, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winchester
Cooper's Casita in Wine Country
4.98 out of 5 average rating, 392 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Superhost
Home in Winchester
Stunning Temecula Wine Country Oasis|Pool|Gameroom
4.87 out of 5 average rating, 134 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Winchester
Temecula Wine Country Home with Pool, Spa, & more!
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 7 beds, 2.5 bathrooms
3–8 Aug
Guest favourite
Home in Winchester
Wine Country Resort - Close to Wineries
4.86 out of 5 average rating, 36 reviews, 5 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Guest suite in Menifee
Adorable guest suite in Menifee.
4.95 out of 5 average rating, 227 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Winchester
6BR｜Pool&SPA｜Mini Golf｜Sauna｜10 Min to Winery
4.97 out of 5 average rating, 36 reviews, 6 bedrooms, 11 beds, 3 bathrooms
2–7 Aug
Guest suite in Winchester
Suite with private entrance near wine country.
4.65 out of 5 average rating, 140 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Jul
Place to stay in Winchester
Master suite+bath, Panoramic View! Close to winery
4.88 out of 5 average rating, 160 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Guest favourite
Home in Menifee
La Casa Bonita: Stay in Style
4.94 out of 5 average rating, 78 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Rooms in Winchester
Spacious Master Suite with 2 rooms & private bath
4.8 out of 5 average rating, 30 reviews, 2 bedrooms, 2 king beds, 1 bathroom
13–18 Jul
Guest suite in Winchester
Guest suite with private entrance, near wineries
4.77 out of 5 average rating, 78 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Guest house in Winchester
The Wine Down Courtyard
4.94 out of 5 average rating, 114 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Home in Winchester
Near Temecula Wine Country! SoCal Home w/ Hot Tub
New place to stay, 5 bedrooms, 5 beds, 3.5 bathrooms
8–13 Jul