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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.97 out of 5 average rating, 689 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 248 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
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
5–10 Jul
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
Top guest favourite
Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
4.99 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Jul
Luxe
Home in Healdsburg
Dry Creek Modern
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
Top guest favourite
Room in Windsor
Wine Country Stay
4.89 out of 5 average rating, 209 reviews, 1 queen bed, 1 bathroom
26–31 Jul
Guest favourite
Guest house in Healdsburg
Walk to Wine Country | Parking | Pilates
4.97 out of 5 average rating, 250 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
4.92 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Aug
Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
4.95 out of 5 average rating, 200 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
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Flat in Healdsburg
Bucher Vineyard Studio
4.99 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 bed, 1 bathroom
15–20 Nov
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
5.0 out of 5 average rating, 64 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
4.93 out of 5 average rating, 473 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 322 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Aug
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Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 487 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest house in Healdsburg
Bunkhouse at Side Road Farm
4.99 out of 5 average rating, 253 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Guest suite in Healdsburg
Jimtown Luxury Suite
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul