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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 254 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
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Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
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Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
4.88 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Superhost
Home in Healdsburg
The Grove on Alexander Valley
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
4.97 out of 5 average rating, 690 reviews, 1 bed, 1 bathroom
27 Oct – 1 Nov