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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 255 reviews
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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, 254 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 367 reviews
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Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 55 reviews
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 180 reviews
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 205 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 100 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Aug
4.88 out of 5 average rating, 66 reviews
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Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 129 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
11–16 Aug
5.0 out of 5 average rating, 164 reviews
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Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 690 reviews
Luxe
Home in Healdsburg
Chalk Hill 360°
4 bedrooms, 4 beds, 3.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 205 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 reviews