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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 private bathrooms
8–13 Sept
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4.98 out of 5 average rating, 124 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
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
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
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 48 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Geyserville
Updated 5 BR house w/ hot tub - walk to downtown!
5 bedrooms, 6 beds
8–13 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Charmer + Hot Tub
2 bedrooms, 3 beds
11–16 Oct
4.99 out of 5 average rating, 75 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
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, 73 reviews
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
8–13 Sept
5.0 out of 5 average rating, 50 reviews
Luxe
Villa in Healdsburg
Wine Country Estate
7 bedrooms, 9 beds
9–14 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
8–13 Sept
4.98 out of 5 average rating, 183 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
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 155 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
11–16 Sept
4.99 out of 5 average rating, 89 reviews
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds
25–30 Oct
4.97 out of 5 average rating, 242 reviews
Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 5 beds
10–15 Nov
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds
9–14 Sept
4.85 out of 5 average rating, 157 reviews