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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
28 Sept – 3 Oct
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4.97 out of 5 average rating, 688 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 248 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
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
4.99 out of 5 average rating, 123 reviews
Top guest favourite
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
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
New place to stay
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 195 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, 83 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 Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
2–7 Jul
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 180 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, 74 reviews
Guest favourite
Home in Healdsburg
Vintage Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
4.87 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
5–10 Jul
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.93 out of 5 average rating, 650 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 133 reviews
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
4.93 out of 5 average rating, 296 reviews