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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, 3 bathrooms
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, 2 bathrooms
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, 2 bathrooms
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, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 268 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
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 68 reviews
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Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
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Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 5 beds, 6 bathrooms
10–15 Nov
4.95 out of 5 average rating, 19 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
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
12–17 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Sept
4.99 out of 5 average rating, 89 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
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, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 16 reviews
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Luxe
Home in Healdsburg
Modern, private Healdsburg oasis
5 bedrooms, 8 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 14 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
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
27 Oct – 1 Nov
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, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 95 reviews
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Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds, 2 bathrooms
20–25 Sept
4.88 out of 5 average rating, 72 reviews