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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 323 reviews
Top guest favourite
Home in Healdsburg
10-acre vineyard with a hot tub
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 254 reviews
Top guest favourite
Home in Healdsburg
Hot tub on 1.5 acres amid vineyards
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Vineyard views from a private redwood deck
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Healdsburg
9-acre estate with pool and vineyard views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Home in Healdsburg
Resort-style pool and sauna near Healdsburg
3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
4.99 out of 5 average rating, 126 reviews
Top guest favourite
Home in Healdsburg
25+ acres with pool and redwood views
6 bedrooms, 7 beds, 3.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Healdsburg
Architect-designed home on a private vineyard
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 180 reviews
Luxe
Home in Healdsburg
New 2024 build with a saltwater pool
3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
26–31 Jul
4.95 out of 5 average rating, 73 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 367 reviews
Guest favourite
Home in Healdsburg
Farmhouse with pool and winery tastings
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 100 reviews
Top guest favourite
Flat in Healdsburg
Art-filled flat near the downtown plaza
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 134 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Home in Geyserville
1870 Victorian estate with pool and vineyard
8 bedrooms, 8 beds, 9 bathrooms
19–24 Jul
5.0 out of 5 average rating, 46 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
2 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
4.99 out of 5 average rating, 81 reviews
Guest favourite
Villa in Healdsburg
Heated pool and vineyard views near downtown
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 66 reviews
Guest favourite
Cottage in Healdsburg
Vineyard views and a hot tub
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 255 reviews