filters

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
,
4.97 out of 5 average rating, 682 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, 246 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
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
9–14 Jul
4.97 out of 5 average rating, 38 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
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 Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
1–6 Jul
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 28 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
Santini Farmhouse - Wine Tastings Included
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.96 out of 5 average rating, 85 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, 54 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
4.95 out of 5 average rating, 61 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
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.97 out of 5 average rating, 133 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
Home in Santa Rosa
Near Healdsburg, Sonoma County Wine Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.93 out of 5 average rating, 72 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
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.92 out of 5 average rating, 253 reviews