filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 29
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
16–21 Nov
,
4.97 out of 5 average rating, 712 reviews
Photo 1 of 15
Featured hotel
Hotel in Healdsburg
Healdsburg Inn on the Plaza, Healdsburg interior .
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 11 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
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 125 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 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 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
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
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds, 7 bathrooms
19–24 Oct
5.0 out of 5 average rating, 18 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, 50 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
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 12
Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 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 24
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
5.0 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
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 78 reviews
Photo 1 of 19
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 141 reviews
Photo 1 of 17
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 496 reviews