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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.95 out of 5 average rating, 221 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 Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
1–6 Sept
4.95 out of 5 average rating, 77 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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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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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
14–19 Sept
4.99 out of 5 average rating, 129 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, 15 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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Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
6–11 Sept
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Superhost
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 5 beds
10–15 Nov
4.94 out of 5 average rating, 18 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
6–11 Sept
4.99 out of 5 average rating, 142 reviews
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Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
20–25 Sept
4.92 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
11–16 Sept
5.0 out of 5 average rating, 52 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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Luxe
Home in Healdsburg
Modern, private Healdsburg oasis
5 bedrooms, 8 beds
21–26 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 102 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
17–22 Oct
4.97 out of 5 average rating, 137 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