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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, 248 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 116 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 84 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
24–29 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 124 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
Top guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
4.99 out of 5 average rating, 74 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
4.9 out of 5 average rating, 91 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 2 beds, 3 bathrooms
25–30 Aug
Luxe
Home in Healdsburg
Chalk Hill 360°
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Luxe
Home in Santa Rosa
Award-Winning Glass House · Pool · Wine Country
New place to stay, 3 bedrooms, 3 beds, 4 bathrooms
19–24 Aug