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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 private bathrooms
31 Oct – 5 Nov
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5.0 out of 5 average rating, 79 reviews
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Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 8 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, 126 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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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, 91 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, 277 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, 51 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, 97 reviews
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
14–19 Nov
4.98 out of 5 average rating, 93 reviews
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Top guest favourite
Home in Geyserville
Updated 5 BR house w/ hot tub - walk to downtown!
5 bedrooms, 6 beds
1–6 Oct
4.99 out of 5 average rating, 143 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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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds
8–13 Nov
4.92 out of 5 average rating, 134 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds
19–24 Oct
5.0 out of 5 average rating, 18 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, 49 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
Modern, private Healdsburg oasis
5 bedrooms, 8 beds
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
1–6 Oct
4.97 out of 5 average rating, 142 reviews
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Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds
25–30 Oct
4.98 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 34 reviews