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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 324 reviews
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
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Superhost
Home in Healdsburg
The Grove on Alexander Valley
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
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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
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
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
4.9 out of 5 average rating, 92 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
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Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
4.93 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 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
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 5 bathrooms
9–14 Aug
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
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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
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Guest house in Healdsburg
Designer Cottage | Garden Oasis | Pilates & Plaza
4.97 out of 5 average rating, 253 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Aug
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Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 3 bathrooms
15–20 Sept
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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
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug