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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 private bathroom
11–16 Oct
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4.85 out of 5 average rating, 96 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 126 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg Plaza Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 75 reviews
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Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 91 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
4.94 out of 5 average rating, 103 reviews
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Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 181 reviews
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Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
3–8 Oct
4.92 out of 5 average rating, 53 reviews
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Luxe
Home in Healdsburg
Farmstay Estate | Pool, Cedar Hot Tub & Honey Farm
4 bedrooms, 4 king beds, 4 bathrooms
6–11 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 275 reviews
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Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds, 3 bathrooms
22–27 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 6 beds, 6 bathrooms
14–19 Nov
4.95 out of 5 average rating, 19 reviews
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Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 97 reviews
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Home in Healdsburg
Fanari Healdsburg | Luxe Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
5–10 Oct
New place to stay
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Top guest favourite
Room in Healdsburg
Modern Vineyard Farmhouse - Cabernet Room
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 45 reviews
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Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 44 reviews