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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 183 reviews
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Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
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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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, 272 reviews
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Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Nov
4.91 out of 5 average rating, 97 reviews
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Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 157 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, 53 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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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.95 out of 5 average rating, 227 reviews
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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, 49 reviews
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Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
7–12 Oct
5.0 out of 5 average rating, 50 reviews
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Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 77 reviews
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Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 10 reviews
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 140 reviews
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Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 712 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.94 out of 5 average rating, 102 reviews
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 168 reviews
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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 90 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.9 out of 5 average rating, 10 reviews