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Search results; Over 1,000 homes in Winchester

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Guest favourite
Cottage in Winchester
Carter's Wine Country Luxury Casita
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.95 out of 5 average rating, 170 reviews
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Top guest favourite
Guest suite in Winchester
Ranch/Separate Private 2 Bdrm Suite w/Patio
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.96 out of 5 average rating, 257 reviews
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Superhost
Home in Winchester
Resort Pool & Spa. Temecula Wine Country Close.
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Winchester
Winchester Place: Temecula Wine Tour/ Pechanga
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Winchester
Temecula Wine Country Home with Pool, Spa, & more!
3 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 51 reviews
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Guest favourite
Home in Winchester
Vineyard Poolside Retreat
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.89 out of 5 average rating, 73 reviews
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Guest favourite
Home in Winchester
6BR｜Pool&SPA｜Mini Golf｜Sauna｜10 Min to Winery
6 bedrooms, 11 beds, 3 bathrooms
4–9 Oct
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Guest house in Winchester
The Wine Down Courtyard
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 130 reviews
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Superhost
Home in Winchester
Luxury Wine Country Retreatl Pool Spa & Game Room
4 bedrooms, 7 beds, 3 bathrooms
25–30 Oct
4.88 out of 5 average rating, 142 reviews
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Guest favourite
Place to stay in Winchester
Downstairs guestroom with private bathroom
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 551 reviews
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Guest favourite
Room in Winchester
Cozy Private Casita
1 bathroom
24–29 Oct
4.92 out of 5 average rating, 396 reviews
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Top guest favourite
Home in Winchester
5 Bedroom Home Just Minutes From Wine Country.
5 bedrooms, 6 beds, 3 bathrooms
3–8 Oct
4.96 out of 5 average rating, 96 reviews
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Bungalow in Winchester
Modern & Spacious Single-Story Home
4 bedrooms, 4 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Winchester
Cooper's Casita in Wine Country
1 bedroom, 1 bed, 1 bathroom
28 Oct – 2 Nov
4.98 out of 5 average rating, 398 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Winchester
TaTa Darling Luxury Wine Country Retreat Near Lake
1 bedroom, 3 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 70 reviews
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Guest favourite
Home in Winchester
Wine Country Resort - Close to Wineries
5 bedrooms, 8 beds, 3 bathrooms
24–29 Oct
4.88 out of 5 average rating, 42 reviews
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Top guest favourite
Guest suite in Winchester
Cozy Casita Getaway
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Guest house in Homeland
Oasis Resort
1 bedroom, 3 beds, 1.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Winchester
French Valley Cozy Retreat
4 bedrooms, 5 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 6 reviews