Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
28 Sept – 3 Oct
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4.97 out of 5 average rating, 682 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 248 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
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
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
Vintage Retreat with Spa in Healdsburg
4.97 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 123 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
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
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 116 reviews, 4 bedrooms, 5 beds, 4 bathrooms
5–10 Jul
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
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 83 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
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
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 201 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
5.0 out of 5 average rating, 37 reviews, 3 bedrooms, 6 beds, 4 bathrooms
16–21 Jul
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
4.99 out of 5 average rating, 73 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
4.98 out of 5 average rating, 125 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 253 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Aug
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
Guest favourite
Home in Healdsburg
Vintage Home in Healdsburg Wine Country
4.87 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul