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Search results; Over 1,000 homes in Healdsburg

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Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.93 out of 5 average rating, 134 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 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
25–30 Oct
5.0 out of 5 average rating, 275 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds
15–20 Nov
4.95 out of 5 average rating, 128 reviews
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Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
3–8 Oct
4.92 out of 5 average rating, 53 reviews
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Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
7–12 Oct
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 50 reviews
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Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 121 reviews
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Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds
25–30 Oct
4.9 out of 5 average rating, 268 reviews
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Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
17–22 Oct
5.0 out of 5 average rating, 96 reviews
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Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds
16–21 Nov
4.93 out of 5 average rating, 302 reviews
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Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 43 reviews
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Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 157 reviews
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Luxe
Home in Healdsburg
Modern, private Healdsburg oasis
5 bedrooms, 8 beds
22–27 Sept
5.0 out of 5 average rating, 15 reviews