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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
8–13 Jul
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4.98 out of 5 average rating, 322 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, 251 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 203 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
4.98 out of 5 average rating, 84 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds, 2 bathrooms
7–12 Aug
4.88 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
4.99 out of 5 average rating, 124 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
7–12 Jul
4.94 out of 5 average rating, 195 reviews
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Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
24–29 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
4.99 out of 5 average rating, 75 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 99 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.84 out of 5 average rating, 89 reviews
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 255 reviews
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
7–12 Jul
4.97 out of 5 average rating, 117 reviews
Luxe
Home in Healdsburg
Chalk Hill 360°
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 65 reviews