filters

Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
,
4.93 out of 5 average rating, 175 reviews
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, 254 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds, 5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 55 reviews
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms, 8 beds, 5 bathrooms
19–24 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 206 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
4.99 out of 5 average rating, 126 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 195 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 66 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 20 reviews