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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
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
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
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
12–17 Jul
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Luxe
Home in Healdsburg
Chalk Hill 360°
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 255 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4.95 out of 5 average rating, 61 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
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
19–24 Jul
Top guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4.97 out of 5 average rating, 231 reviews, 4 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 3 bathrooms
25–30 Aug