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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 272 reviews
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
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, 124 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
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.96 out of 5 average rating, 85 reviews
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, 49 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 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
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
4–9 Oct
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
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
Top guest favourite
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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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
12–17 Sept
4.99 out of 5 average rating, 89 reviews
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Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
3 bedrooms, 4 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.9 out of 5 average rating, 40 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
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 96 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
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews