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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.93 out of 5 average rating, 134 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 124 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, 272 reviews
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
13–18 Oct
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
21–26 Sept
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
22–27 Nov
4.91 out of 5 average rating, 97 reviews
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds
21–26 Sept
New place to stay
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds
15–20 Oct
4.99 out of 5 average rating, 72 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
17–22 Oct
5.0 out of 5 average rating, 96 reviews
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
3 bedrooms, 4 beds
29 Oct – 3 Nov
4.9 out of 5 average rating, 40 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
20–25 Sept
4.99 out of 5 average rating, 90 reviews
Luxe
Villa in Healdsburg
Sonoma Estate: Tennis, Pickleball, Pool, Privacy
7 bedrooms, 9 beds
15–20 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 74 reviews
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 157 reviews