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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
Dry Creek Valley Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.96 out of 5 average rating, 489 reviews
Top guest favourite
Home in Healdsburg
10-acre vineyard with a hot tub
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
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Vineyard views from a private redwood deck
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
25+ acres with pool and redwood 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
Glass-enclosed fireplace on a house-length deck
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Healdsburg
Wine tastings included, hot tub, and arcades
4.95 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 367 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 255 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
4.97 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 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
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
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
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
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
Top guest favourite
Guest house in Healdsburg
Walk to wine country with Pilates studio
4.97 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug