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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
16–21 Nov
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4.97 out of 5 average rating, 712 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg Inn on the Plaza, Healdsburg interior .
1 bedroom, 1 king bed
26–31 Oct
4.91 out of 5 average rating, 11 reviews
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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, 8 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 126 reviews
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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds
8–13 Nov
4.92 out of 5 average rating, 134 reviews
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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, 53 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds
19–24 Oct
5.0 out of 5 average rating, 18 reviews
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Luxe
Home in Healdsburg
Farmstay Estate | Pool, Cedar Hot Tub & Honey Farm
4 bedrooms, 4 king beds
6–11 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 bedroom, 1 queen bed
4–9 Oct
4.97 out of 5 average rating, 72 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
10–15 Oct
4.94 out of 5 average rating, 103 reviews
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Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 79 reviews
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Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
4–9 Oct
4.99 out of 5 average rating, 91 reviews
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Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
3–8 Oct
4.97 out of 5 average rating, 142 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 54 reviews
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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, 97 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 184 reviews
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Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed
11–16 Oct
4.96 out of 5 average rating, 497 reviews