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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 323 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Healdsburg
Hot tub on 1.5 acres amid vineyards
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
9-acre estate with pool and vineyard views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
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
Superhost
Home in Healdsburg
Vineyard villa with pool and wine tastings
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
19–24 Jul
Luxe
Home in Healdsburg
Dry Creek Wonderland | Private Farm Estate in Wine
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Top guest favourite
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
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
Top guest favourite
Guest house in Healdsburg
Vineyard views and a private hot tub
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Cottage in Healdsburg
Vineyard-surrounded with a fire pit
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Healdsburg
Private vineyard with complimentary winery tastings
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 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
Treehouse in Bodega Bay
Redwood treehouse 30 feet up on a ranch
4.96 out of 5 average rating, 224 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Oct
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
Guest favourite
Villa in Healdsburg
Wine-country views with 13-foot ceilings
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Luxe
Home in Healdsburg
New 2024 build with a saltwater pool
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Healdsburg
Modern farmhouse with complimentary wine tastings
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Oct
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul