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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 private bathrooms
22–27 Sept
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4.97 out of 5 average rating, 30 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
13–18 Sept
4.94 out of 5 average rating, 102 reviews
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
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
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
4–9 Oct
5.0 out of 5 average rating, 50 reviews
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds
21–26 Sept
New place to stay
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
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, 9 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
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
22–27 Oct
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
3–8 Oct
4.92 out of 5 average rating, 52 reviews