filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 29
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 private bathrooms
4–9 Oct
,
5.0 out of 5 average rating, 125 reviews
Photo 1 of 15
Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 11 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
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 75 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, 43 reviews
Photo 1 of 29
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.96 out of 5 average rating, 67 reviews
Photo 1 of 16
Top guest favourite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 72 reviews
Photo 1 of 10
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 91 reviews
Photo 1 of 29
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 181 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
4.94 out of 5 average rating, 102 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.92 out of 5 average rating, 134 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 6
Top guest favourite
Room in Healdsburg
Modern Vineyard Farmhouse - Cabernet Room
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 45 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 29
Luxe
Home in Healdsburg
Farmstay Estate | Pool, Cedar Hot Tub & Honey Farm
4 bedrooms, 4 king beds, 4 bathrooms
6–11 Nov
5.0 out of 5 average rating, 14 reviews
Photo 1 of 29
Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms, 6 beds, 6 bathrooms
14–19 Nov
4.95 out of 5 average rating, 19 reviews
Photo 1 of 29
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
5–10 Oct
New place to stay
Photo 1 of 29
Guest favourite
Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.88 out of 5 average rating, 60 reviews