filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 29
Top guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 bed, 1 private bathroom
24–29 Oct
,
4.93 out of 5 average rating, 484 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 House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 126 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
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 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
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 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 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
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 27
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 54 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, 129 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, 93 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 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, 142 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 29
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 77 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 11 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 712 reviews