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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 private bathrooms
25–30 Oct
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4.96 out of 5 average rating, 98 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
Top guest favourite
Home in Healdsburg
Hot tub on 1.5 acres amid vineyards
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 28 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Luxe
Home in Healdsburg
New 2024 build with a saltwater pool
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Forestville
Midcentury-modern with 14-foot vaulted ceilings
4.99 out of 5 average rating, 367 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
Top guest favourite
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
9–14 Aug
Guest favourite
Cottage in Healdsburg
Vineyard views and a hot tub
4.92 out of 5 average rating, 255 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
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
Top guest favourite
Flat in Healdsburg
Art-filled flat near the downtown plaza
4.97 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Villa in Healdsburg
Wine-country views with 13-foot ceilings
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Guest favourite
Holiday home in Healdsburg
2 blocks from the Plaza
4.97 out of 5 average rating, 109 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 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
Guest favourite
Villa in Healdsburg
Heated pool and vineyard views near downtown
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Guest house in Healdsburg
Vineyard views and a private hot tub
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Superhost
Home in Geyserville
Vineyard estate with pool and winery tastings
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug