filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 23
Top guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 private bathroom
11–16 Oct
,
4.85 out of 5 average rating, 96 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 7 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 275 reviews
Photo 1 of 24
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 49 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds, 3 bathrooms
15–20 Nov
4.95 out of 5 average rating, 127 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
3–8 Oct
4.92 out of 5 average rating, 53 reviews
Photo 1 of 13
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 157 reviews
Photo 1 of 29
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
7–12 Oct
5.0 out of 5 average rating, 50 reviews
Photo 1 of 29
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 121 reviews
Photo 1 of 24
Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds, 2.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 64 reviews
Photo 1 of 29
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
Photo 1 of 29
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 74 reviews
Photo 1 of 20
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.98 out of 5 average rating, 91 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Nov
4.9 out of 5 average rating, 98 reviews
Photo 1 of 29
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 96 reviews
Photo 1 of 19
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 140 reviews