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Search results; Over 1,000 homes in Healdsburg

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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, 275 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
4–9 Oct
5.0 out of 5 average rating, 125 reviews
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Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
4–9 Oct
4.99 out of 5 average rating, 90 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 Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
4–9 Oct
4.95 out of 5 average rating, 77 reviews
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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds
26–31 Oct
4.92 out of 5 average rating, 134 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 184 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
14–19 Nov
4.98 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
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Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
16–21 Nov
4.97 out of 5 average rating, 712 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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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, 129 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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Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
22–27 Nov
4.9 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Healdsburg
Spectacular Healdsburg Manor-6beds/4.5B, POOL+SPA!
6 bedrooms, 5 beds
2–7 Nov
5.0 out of 5 average rating, 48 reviews
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Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds
5–10 Oct
4.98 out of 5 average rating, 65 reviews