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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
28 Sept – 3 Oct
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4.97 out of 5 average rating, 688 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 248 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 116 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 202 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
24–29 Jul
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 99 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
5–10 Jul
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 48 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
4.99 out of 5 average rating, 74 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
16–21 Jul
5.0 out of 5 average rating, 37 reviews
Luxe
Home in Healdsburg
Chalk Hill 360°
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.84 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
4.95 out of 5 average rating, 61 reviews