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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Guest house in Healdsburg
Romantic Cottage | Walk to Healdsburg Plaza
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.94 out of 5 average rating, 388 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 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
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
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 54 reviews
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Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 121 reviews
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Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds, 7 bathrooms
25–30 Sept
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
5 bedrooms, 6 beds, 3 bathrooms
15–20 Nov
4.95 out of 5 average rating, 128 reviews
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Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 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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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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Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
23–28 Sept
New place to stay
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Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 96 reviews
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Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds, 3 bathrooms
22–27 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Healdsburg
Wine Country Retreat - Modern Luxury Estate
4 bedrooms, 4 beds, 3.5 bathrooms
26–31 Oct
4.94 out of 5 average rating, 31 reviews