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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
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4.97 out of 5 average rating, 29 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 183 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 271 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Sept
4.99 out of 5 average rating, 89 reviews
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 133 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Oct
4.99 out of 5 average rating, 72 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
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Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
20–25 Oct
4.99 out of 5 average rating, 182 reviews
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Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.99 out of 5 average rating, 138 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 102 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 259 reviews
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.93 out of 5 average rating, 481 reviews
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
7–12 Sept
4.91 out of 5 average rating, 176 reviews
Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 214 reviews