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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.97 out of 5 average rating, 696 reviews
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, 257 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
1–6 Aug
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds
3–8 Oct
4.99 out of 5 average rating, 368 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
3–8 Aug
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
3 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
3–8 Aug
4.9 out of 5 average rating, 92 reviews
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds
4–9 Oct
4.93 out of 5 average rating, 175 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
2 bedrooms, 2 queen beds
15–20 Sept
5.0 out of 5 average rating, 32 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
23–28 Aug
4.97 out of 5 average rating, 117 reviews
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds
2–7 Aug
4.84 out of 5 average rating, 90 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds
15–20 Aug
4.95 out of 5 average rating, 62 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
2–7 Aug
4.92 out of 5 average rating, 48 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds
6–11 Sept
4.92 out of 5 average rating, 256 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds
11–16 Sept
4.92 out of 5 average rating, 131 reviews