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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 shared bathroom
13–18 Sept
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4.96 out of 5 average rating, 112 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
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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, 272 reviews
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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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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, 48 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 96 reviews
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 155 reviews
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Home in Geyserville
Updated 5 BR house w/ hot tub - walk to downtown!
5 bedrooms, 6 beds, 3 bathrooms
9–14 Sept
4.99 out of 5 average rating, 142 reviews
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.98 out of 5 average rating, 183 reviews
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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Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
9–14 Sept
5.0 out of 5 average rating, 50 reviews
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Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
22–27 Oct
4.99 out of 5 average rating, 76 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
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Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
14–19 Sept
4.95 out of 5 average rating, 77 reviews
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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, 77 reviews
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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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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, 52 reviews
Guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds, 1.5 bathrooms
10–15 Sept
4.85 out of 5 average rating, 157 reviews
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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