filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 29
Luxe
Home in Healdsburg
Mill Creek - AvantStay | Patio, Hot Tub, A+ Design
2 bedrooms, 3 beds, 2.5 private bathrooms
18–23 Oct
,
4.89 out of 5 average rating, 55 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 125 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
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
25–30 Oct
5.0 out of 5 average rating, 275 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
Guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds
14–19 Nov
4.93 out of 5 average rating, 181 reviews
Photo 1 of 24
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
Photo 1 of 13
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
Photo 1 of 29
Luxe
Home in Healdsburg
Modern, private Healdsburg oasis
5 bedrooms, 8 beds
21–26 Sept
5.0 out of 5 average rating, 14 reviews
Photo 1 of 29
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds
24–29 Sept
New place to stay
Photo 1 of 29
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
21–26 Sept
4.94 out of 5 average rating, 102 reviews
Photo 1 of 29
Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds
18–23 Sept
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds
15–20 Nov
4.95 out of 5 average rating, 127 reviews
Photo 1 of 24
Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds
11–16 Oct
4.98 out of 5 average rating, 64 reviews
Photo 1 of 29
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, 53 reviews
Photo 1 of 29
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
Photo 1 of 29
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