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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Aug
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4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Santa Rosa
Spacious Luxurious Modern Home with Great Views
4.9 out of 5 average rating, 99 reviews, 7 bedrooms, 7 beds, 7.5 bathrooms
2–7 Aug
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 257 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 3 bathrooms
20–25 Oct
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 257 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 368 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
4.93 out of 5 average rating, 176 reviews, 3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
4.98 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4.86 out of 5 average rating, 156 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Aug
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
4.84 out of 5 average rating, 90 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4.95 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4 bathrooms
15–20 Aug
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
4.99 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 119 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug