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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Santini Farmhouse - Wine Tastings Included
2 bedrooms, 3 beds, 2 shared bathrooms
20–25 Jul
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4.96 out of 5 average rating, 85 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
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
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
21–26 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds
20–25 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
17–22 Jul
4.98 out of 5 average rating, 181 reviews
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms, 8 beds
19–24 Jul
New place to stay
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
10–15 Aug
4.99 out of 5 average rating, 126 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds
19–24 Jul
4.92 out of 5 average rating, 131 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds
19–24 Jul
4.94 out of 5 average rating, 195 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds
3–8 Oct
4.99 out of 5 average rating, 368 reviews
Guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 206 reviews
Top guest favourite
Guest suite in Healdsburg
Jimtown Luxury Suite
1 bedroom, 1 king bed
17–22 Jul
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
26–31 Jul
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 20 reviews