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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 254 reviews
Top guest favourite
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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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
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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
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Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
4.96 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Room in Santa Rosa
Golf Course Sanctuary-Designed for Travel Nurses
New place to stay, 1 queen bed, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 86 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
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Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 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
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 368 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
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Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 131 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
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Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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Home in Geyserville
Historic Home; Walk to Cyrus, Diavola, Catelli's
4.98 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 4 bathrooms
21–26 Jul
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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
Guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 90 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
Guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 208 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Healdsburg
Santini Farmhouse - Wine Tastings Included
4.96 out of 5 average rating, 85 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug