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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 253 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 204 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 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
11–16 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Jul
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Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Luxe
Home in Healdsburg
Chalk Hill 360°
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 125 reviews, 3 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
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Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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
19–24 Jul
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Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 3 bathrooms
25–30 Aug
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Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
4.92 out of 5 average rating, 48 reviews, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
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Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
5.0 out of 5 average rating, 94 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul