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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds, 1.5 private bathrooms
10–15 Jul
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4.86 out of 5 average rating, 156 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 248 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 116 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 84 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 163 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
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Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 124 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
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Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
24–29 Jul
Guest favourite
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
6–11 Jul
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Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
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Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
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Home in Healdsburg
Casa Pavone, by Vinifera Homes
4.88 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
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Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
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Home in Healdsburg
Vineyard Vue - Wine Tastings Included
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
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Guest suite in Healdsburg
Jimtown Luxury Suite
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 116 reviews, 4 bedrooms, 5 beds, 4 bathrooms
6–11 Jul
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul