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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.95 out of 5 average rating, 227 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 124 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 272 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed
1–6 Nov
4.97 out of 5 average rating, 260 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
14–19 Sept
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
14–19 Sept
4.95 out of 5 average rating, 77 reviews
Luxe
Villa in Healdsburg
Stunning Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds
15–20 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 183 reviews
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds
21–26 Sept
New place to stay
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 157 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 10 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
17–22 Oct
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
7–12 Oct
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews
Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds
16–21 Nov
4.93 out of 5 average rating, 302 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 42 reviews