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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, 2 bathrooms
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, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 125 reviews
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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, 90 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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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 78 reviews
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Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
7–12 Oct
5.0 out of 5 average rating, 50 reviews
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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.92 out of 5 average rating, 134 reviews
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.98 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 77 reviews
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Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds, 3 bathrooms
15–20 Nov
4.95 out of 5 average rating, 129 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
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 54 reviews
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 141 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
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Top guest favourite
Home in Healdsburg
Spectacular Healdsburg Manor-6beds/4.5B, POOL+SPA!
6 bedrooms, 5 beds, 4.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 48 reviews
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Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
5–10 Oct
New place to stay
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 50 reviews