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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, 323 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 254 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
21–26 Oct
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
21–26 Jul
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 207 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds
24–29 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds
25–30 Oct
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
26–31 Jul
New place to stay
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds
24–29 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
26–31 Aug
4.98 out of 5 average rating, 358 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
26–31 Jul
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed
27 Jul – 1 Aug
4.99 out of 5 average rating, 131 reviews
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms, 8 beds
19–24 Jul
New place to stay
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds
3–8 Oct
4.99 out of 5 average rating, 368 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
10–15 Aug
4.99 out of 5 average rating, 127 reviews
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 253 reviews