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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 private bathrooms
17–22 Oct
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4.96 out of 5 average rating, 96 reviews
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
5.0 out of 5 average rating, 9 reviews, 1 bed, 2 bathrooms
5–10 Jul
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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
4–9 Oct
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 Geyserville
Luxurious Wine Country Estate
5.0 out of 5 average rating, 46 reviews, 8 bedrooms, 8 beds, 9 bathrooms
1–6 Jul
Guest favourite
Guest house in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard
4.97 out of 5 average rating, 249 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 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
5–10 Jul
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Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
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Farm stay in Geyserville
Country Barn in Downtown Geyserville
4.99 out of 5 average rating, 173 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
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Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
4.99 out of 5 average rating, 312 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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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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Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 486 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Healdsburg
Views, hot tub, sauna, cold plunge, cinema!
4.98 out of 5 average rating, 120 reviews, 2 bedrooms, 3 beds, 3 bathrooms
13–18 Jul
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Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4.95 out of 5 average rating, 61 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
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Flat in Healdsburg
Bucher Vineyard Studio
4.99 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
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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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Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Healdsburg
Vintage Home in Healdsburg Wine Country
4.87 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul