filters

Search results; Over 1,000 homes in Healdsburg

Photo 1 of 19
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
,
4.97 out of 5 average rating, 141 reviews
Photo 1 of 29
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
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 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
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds
25–30 Oct
4.9 out of 5 average rating, 268 reviews
Photo 1 of 27
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 54 reviews
Photo 1 of 29
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 77 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, 65 reviews
Photo 1 of 29
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
7–12 Oct
5.0 out of 5 average rating, 50 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 29
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
4–9 Oct
4.96 out of 5 average rating, 67 reviews
Photo 1 of 29
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
22–27 Nov
4.9 out of 5 average rating, 98 reviews
Photo 1 of 20
Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds
16–21 Nov
4.93 out of 5 average rating, 302 reviews
Photo 1 of 29
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 121 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
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, 128 reviews
Photo 1 of 27
Top guest favourite
Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed
4–9 Oct
4.94 out of 5 average rating, 374 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 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