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Search results; Over 1,000 homes in Healdsburg

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Guest favourite
Cottage in Healdsburg
Luxury 1-br cottage on 30-acre Healdsburg vineyard
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.97 out of 5 average rating, 38 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 122 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 77 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, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 268 reviews
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Oct
4.98 out of 5 average rating, 47 reviews
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Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
6–11 Sept
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Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.99 out of 5 average rating, 129 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 52 reviews
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Luxe
Villa in Healdsburg
Wine Country Estate
5 bedrooms, 6 beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 15 reviews
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Superhost
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 5 beds, 6 bathrooms
10–15 Nov
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds, 3 bathrooms
6–11 Sept
4.95 out of 5 average rating, 126 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, 3 bathrooms
6–11 Sept
4.99 out of 5 average rating, 142 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 137 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 102 reviews
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Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
20–25 Sept
4.92 out of 5 average rating, 51 reviews
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Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 84 reviews
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Superhost
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 74 reviews