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Search results; Over 1,000 homes in Healdsburg

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Guest favourite
Cabin in Healdsburg
Updated Russian River Cabin (beach/river access!)
2 bedrooms, 4 beds, 1.5 private bathrooms
1–6 Oct
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4.96 out of 5 average rating, 190 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg Inn on the Plaza, Healdsburg interior .
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 125 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds, 7 bathrooms
19–24 Oct
5.0 out of 5 average rating, 18 reviews
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Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 184 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, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
4–9 Oct
4.99 out of 5 average rating, 90 reviews
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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, 43 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
4.94 out of 5 average rating, 102 reviews
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Luxe
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
3 bedrooms, 3 king beds, 2.5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 65 reviews
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Top guest favourite
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, 275 reviews
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Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 181 reviews
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Top guest favourite
Room in Healdsburg
Modern Vineyard Farmhouse - Cabernet Room
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 45 reviews
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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
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, 4 bathrooms
3–8 Oct
4.92 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 50 reviews
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Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
5–10 Oct
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