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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 private bathrooms
7–12 Sept
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4.98 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 6 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, 47 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, 268 reviews
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Guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed
20–25 Sept
4.97 out of 5 average rating, 256 reviews
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Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 130 reviews
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Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
12–17 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
6–11 Sept
4.98 out of 5 average rating, 183 reviews
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Luxe
Villa in Healdsburg
Wine Country Estate
5 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds
6–11 Sept
4.95 out of 5 average rating, 126 reviews
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Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 75 reviews
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Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
6–11 Sept
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Top guest favourite
Cottage in Healdsburg
Creekside Cottage
2 bedrooms, 3 beds
4–9 Oct
4.96 out of 5 average rating, 92 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, 53 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, 42 reviews
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Top guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds
7–12 Sept
4.97 out of 5 average rating, 241 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
27 Oct – 1 Nov
4.97 out of 5 average rating, 137 reviews