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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 253 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, 85 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 204 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 117 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, 100 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
11–16 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
4.99 out of 5 average rating, 125 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 61 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, 16 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 48 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Jul
4.94 out of 5 average rating, 195 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
New place to stay
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.84 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
4.92 out of 5 average rating, 48 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
4.97 out of 5 average rating, 117 reviews
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 129 reviews