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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 255 reviews
Top guest favourite
Home in Healdsburg
Architect-designed home on a private vineyard
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Home in Healdsburg
Vineyard views from Montage Healdsburg Resort
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 323 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Aug
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Guest suite in Healdsburg
Vineyard estate with Mt. St. Helena views
4.93 out of 5 average rating, 475 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 489 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
5.0 out of 5 average rating, 9 reviews, 1 bed, 2 bathrooms
2–7 Aug
Top guest favourite
Guest house in Healdsburg
Gourmet breakfast on a private patio
4.95 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
Top guest favourite
Room in Windsor
Walk to shops in wine country
4.9 out of 5 average rating, 210 reviews, 1 queen bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest house in Healdsburg
Walk to wine country with Pilates studio
4.97 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
4.88 out of 5 average rating, 57 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Guest house in Healdsburg
Gated cottage with a private hot tub
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
4.92 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Healdsburg
Vineyard views from a 2-acre farmhouse
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
4.99 out of 5 average rating, 81 reviews, 2 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
Guest favourite
Home in Forestville
Midcentury-modern with 14-foot vaulted ceilings
4.99 out of 5 average rating, 367 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct