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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, 257 reviews
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds
19–24 Aug
4.98 out of 5 average rating, 324 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.96 out of 5 average rating, 489 reviews
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed
10–15 Aug
5.0 out of 5 average rating, 10 reviews
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Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds
4–9 Aug
4.97 out of 5 average rating, 253 reviews
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Guest suite in Healdsburg
Jimtown Luxury Suite
1 bedroom, 1 king bed
27 Aug – 1 Sept
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
3–8 Aug
4.98 out of 5 average rating, 56 reviews
Guest favourite
Place to stay in Healdsburg
Modern Vineyard Farmhouse - Zinfandel Room
1 bedroom, 1 bed
1–6 Aug
4.98 out of 5 average rating, 41 reviews
Home in Healdsburg
Great outdoor space, fire pit & gourmet kitchen
1 bedroom, 1 queen bed
21–28 Nov
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
1 bedroom, 1 bed
2–7 Aug
5.0 out of 5 average rating, 67 reviews
Guest favourite
Home in Healdsburg
Spacious Healdsburg Home - Walk to the Square!
3 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
8–13 Aug
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds
1–6 Aug
4.98 out of 5 average rating, 120 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds
2–7 Aug
4.93 out of 5 average rating, 651 reviews
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 42 reviews
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Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed
9–14 Aug
4.99 out of 5 average rating, 129 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed
20–25 Aug
4.92 out of 5 average rating, 100 reviews
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds
1–6 Aug
5.0 out of 5 average rating, 3 reviews