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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 private bathroom
27 Jul – 1 Aug
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4.97 out of 5 average rating, 253 reviews
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
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Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
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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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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 206 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
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
26–31 Jul
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 6 beds, 5 bathrooms
24–29 Jul
Top guest favourite
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
21–26 Oct
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Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
4.96 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
19–24 Jul
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 131 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 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
Guest favourite
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
4.95 out of 5 average rating, 226 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Nov
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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
11–16 Aug
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 29 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 126 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug