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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 private bathrooms
17–22 Oct
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4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 248 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 116 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 123 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
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Home in Geyserville
Luxurious Wine Country Estate
5.0 out of 5 average rating, 46 reviews, 8 bedrooms, 8 beds, 9 bathrooms
2–7 Jul
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 162 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 83 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
4.93 out of 5 average rating, 650 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Superhost
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Luxe
Home in Healdsburg
Dry Creek Modern
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Jul
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 50 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
4.97 out of 5 average rating, 79 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul