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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 private bathroom
11–16 Aug
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4.92 out of 5 average rating, 149 reviews
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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
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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
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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
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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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
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Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 28 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
4.97 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
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Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4.95 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
4.97 out of 5 average rating, 109 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
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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
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 126 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 255 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
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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
19–24 Jul
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 367 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
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Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul