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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.97 out of 5 average rating, 690 reviews
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, 254 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
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
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Superhost
Home in Santa Rosa
Glass-enclosed fireplace on a house-length deck
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Healdsburg
Wine tastings included, hot tub, and arcades
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
4.95 out of 5 average rating, 62 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
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 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
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
Guest house in Healdsburg
Vineyard views and a private hot tub
1 bedroom, 1 king bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 164 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
Guest favourite
Holiday home in Healdsburg
2 blocks from the Plaza
2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 109 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
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
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
31 Jul – 5 Aug
4.93 out of 5 average rating, 650 reviews
Luxe
Villa in Healdsburg
Hilltop vineyard views with pool and hot tub
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 251 reviews