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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest suite in Healdsburg
Jimtown Luxury Suite
1 bedroom, 1 bed, 1 private bathroom
11–16 Nov
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5.0 out of 5 average rating, 97 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 183 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
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Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 6 reviews
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Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds
13–18 Sept
4.92 out of 5 average rating, 133 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
13–18 Sept
4.99 out of 5 average rating, 90 reviews
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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
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, 73 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
22–27 Oct
4.99 out of 5 average rating, 76 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
13–18 Sept
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
Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds
5–10 Oct
4.98 out of 5 average rating, 64 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 42 reviews
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Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds
14–19 Nov
4.93 out of 5 average rating, 180 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds
14–19 Sept
4.91 out of 5 average rating, 176 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
3–8 Oct
4.92 out of 5 average rating, 52 reviews