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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 256 reviews
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 323 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Aug
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Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 489 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
4.97 out of 5 average rating, 253 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
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Room in Santa Rosa
Lovely older home w/ private rm and bath/tub.
4.86 out of 5 average rating, 894 reviews, 1 single bed, 1 bathroom
26–31 Jul
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Holiday home in Healdsburg
Downtown Healdsburg Nest
4.97 out of 5 average rating, 109 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
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Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
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Guest house in Healdsburg
The Roost - Sun Room
4.94 out of 5 average rating, 368 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
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Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
4.99 out of 5 average rating, 71 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
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Home in Healdsburg
Healdsburg Garden House
4.93 out of 5 average rating, 650 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
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Flat in Healdsburg
Bucher Vineyard Studio
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
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Room in Windsor
Rivermind, a Wine Country Retreat #1
4.93 out of 5 average rating, 164 reviews, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
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Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
4.95 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Sept
Guest favourite
Place to stay in Healdsburg
Modern Vineyard Farmhouse - Zinfandel Room
4.98 out of 5 average rating, 41 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Jul